2-aryl cyclopentane-1,3-dione derivatives

ABSTRACT

PCT No. PCT/EP95/02482 Sec. 371 Date Dec. 31, 1996 Sec. 102(e) Date Dec. 31, 1996 PCT Filed Jun. 26, 1995 PCT Pub. No. WO96/01798 PCT Pub. Date Jan. 25, 1996The present invention relates to novel 2-aryl-3-hydroxy-cyclopent-2-en-1-one derivatives of the formula (I)    &lt;IMAGE&gt;  (I)  in which X represents halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy, Y represents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy, Z represents halogen, nitro, cyano, alkyl, alkoxy or halogenoalkoxy and A, B, D1, D2, G and n have the meaning given in the description, several processes for their preparation and their use as compositions for controlling pests and as herbicides.

This application is a 371 of PCT/EP95/02482, filed Jun. 26, 1995.

The present invention relates to novel 2-aryl-3-hydroxy-Δ²-cyclopenten-1-one derivatives, processes for their preparation andtheir use as herbicides and pest control agents.

It is known that certain substituted 2-arylcyclopentanediones haveherbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos.4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547 and 4,632,698).Similarly substituted compounds are furthermore known;3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-en-1-one from the publicationMicklefield et al., Tetrahedron, (1992), 7519-26 and the naturalsubstance involutin,(-)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-)4-hydroxy-phenyl)-cyclopent-2-enonefrom the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. Noinsecticidal or acaricidal action is described.

Novel 2-aryl-3-hydroxy-cyclopent-2-en-1-one derivatives of the formula(I) ##STR2## in which x represents halogen, nitro, cyano, alkyl, alkoxy,alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl orhalogenoalkoxy,

Y represents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy,alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl orhalogenoalkoxy,

Z represents halogen, nitro, cyano, alkyl, alkoxy or halogenoalkoxy,

n represents an integer from 0 to 3, or wherein the radicals X and Z,together with the phenyl radical to which they are bonded, form thenaphthalene radical of the formula ##STR3## in which Y has theabovementioned meaning,

A and B independently of one another represent alkyl, alkenyl, alkinyl,alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, in each case optionallysubstituted once or several times in an identical or different manner byhalogen, or saturated or unsaturated, unsubstituted or substitutedcycloalkyl which is optionally interrupted by at least one heteroatom,or phenyl or phenylalkyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, alkyl,halogenoalkyl, alkoxy, halogenoalkoxy, cyano or nitro,

or

A and B, together with the carbon atom to which they are bonded, form asaturated or unsaturated ring which is optionally interrupted by atleast one heteroatom and is optionally substituted,

or

A and B, together with the carbon atom to which they are bonded, form aring in which two substituents, together with the carbon atoms to whichthey are bonded, form a saturated or unsaturated ring which isoptionally substituted once or several times in an identical ordifferent manner by halogen, alkyl or alkoxy and can contain oxygen orsulphur,

D¹ and D² independently of one another represent hydrogen, halogen oralkyl which is optionally substituted by halogen or optionallysubstituted phenyl,

G represents hydrogen (a), or represents one of the groups ##STR4## Erepresents a metal ion equivalent or an ammonium ion, L representsoxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, in each case optionally substituted once or severaltimes in an identical or different manner by halogen, or optionallysubstituted, saturated or unsaturated cycloalkyl, which can beinterrupted by at least one heteroatom, or represents in each caseoptionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

R² represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, in eachcase optionally substituted once or several times in an identical ordifferent manner by halogen, or in each case optionally substitutedcycloalkyl, phenyl or benzyl,

R³ represents alkyl which is in each case optionally substituted once orseveral times in an identical or different manner by halogen, orrepresents in each case optionally substituted phenyl or phenylalkyl,

R⁴ and R⁵ independently of one another represent alkyl, alkoxy,alkylamino, alkenylamino, dialkylamino, dialkenylamino, alkylthio,alkenylthio, alkinylthio or cycloalkylthio, in each case optionallysubstituted once or several times in an identical or different manner byhalogen, or represent in each case optionally substituted phenyl,phenoxy or phenylthio,

R⁶ and R⁷ independently of one another represent hydrogen or alkyl,alkenyl, alkoxy or alkoxyalkyl, in each case optionally substituted onceor several times in an identical or different manner by halogen, orrepresent optionally substituted phenyl or optionally substitutedbenzyl,

or

R⁶ and R⁷ together represent an alkylene radical which is optionallyinterrupted by oxygen or sulphur,

and the enantiomerically pure forms of compounds of the formula (I) havenow been found.

Depending on the position of the substituent G, the compounds of theformula (I) can be present in the two isomeric forms of the formula I-Aand I-B ##STR5## which the broken line in the formula (I) is intended toillustrate.

The compounds of the formulae I-A and I-B can be present both asmixtures and in the form of their pure isomers. If appropriate, mixturesof the compounds of the formulae I-A and I-B can be separated byphysical methods, for example by chromatographic methods.

For reasons of better clarity, in the following in each case only one ofthe possible isomers is shown. This does not exclude the possibilitythat the compounds, where appropriate, are present in the form of theisomer mixtures or in the other respective isomeric form.

Incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g)of the group G, the following main structures (Ia) to (Ig) result:##STR6## wherein A, B, D¹, D², E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶,R⁷ and n have the abovementioned meanings.

It has furthermore been found

(A)

that compounds of the formula (Ia) ##STR7## in which A, B, D¹, D², X, Y,Z and n have the abovementioned meaning,

are obtained when

ketocarboxylic acid esters of the formula (II) ##STR8## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning

and

R⁸ represents alkyl (in particular C₁ -C₈ -alkyl),

are subjected to intermolecular cyclization, if appropriate in thepresence of a diluent and in the presence of a base, and

(B)

that compounds of the formula (Ib) ##STR9## in which A, B, D¹, D², X, Y,Z, R¹ and n have the abovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR10## in which A, B,D¹, D², X Y, Z and n have the abovementioned meaning,

α) are reacted with acid halides of the formula (III) ##STR11## in whichR¹ has the abovementioned meaning

and

Hal represents halogen (in particular chlorine or bromine),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent,

or

β) are reacted with carboxylic acid anhydrides of the formula (IV)

    R.sup.1 --CO--O--CO--R.sup.1                               (IV)

in which

R¹ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent,

and

(C)

that compounds of the formula (Ic) ##STR12## in which A, B, D¹, D², X,Y, Z, R² and n have the abovementioned meaning,

L represents oxygen and

M represents oxygen or sulphur,

are obtained when compounds of the formula (Ia) ##STR13## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning,

are reacted with a chloroformic acid ester or chloroformic acid thiolester of the formula (V)

    R.sup.2 --M--CO--Cl                                        (V)

in which

R² and M have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, and

(D)

that compounds of the formula (Ic) ##STR14## in which A, B, D¹, D², R²,X, Y, Z and n have the abovementioned meaning,

L represents sulphur and

M represents oxygen or sulphur,

are obtained when compounds of the formula (Ia) ##STR15## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning,

α) are reacted with a chloromonothioformic acid ester orchlorodithioformic acid ester of the formula (VI) ##STR16## in which Mand R² have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, or

β) are reacted with carbon disulphide and then with alkyl halides of theformula (VII)

    R.sup.2 -Hal                                               (VII)

in which

R² has the abovementioned meaning

and

Hal represents chlorine, bromine or iodine,

if appropriate in the presence of a diluent and if appropriate in thepresence of a base, and

(E)

that compounds of the formula (Id) ##STR17## in which A, B, D¹, D², X Y,Z, R³ and n have the abovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR18## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning,

are reacted with sulphonic acid chlorides of the formula (VIII)

    R.sup.3 --SO.sub.2 --Cl                                    (VIII)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, and

(F)

that compounds of the formula (Ie) ##STR19## in which A, B, D¹, D², L,X, Y, Z, R⁴, R⁵ and n have the abovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR20## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning,

are reacted with phosphorus compounds of the formula (IX) ##STR21## inwhich L, R⁴ and R⁵ have the abovementioned meaning and

Hal represents halogen (in particular chlorine or bromine),

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, and

(G)

that compounds of the formula (If) ##STR22## in which A, B, D¹, D², L,X, Y, Z, R⁶, R⁷ and n have the abovementioned meaning,

are obtained when compounds of the formula (Ia) ##STR23## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning,

α) are reacted with isocyanates or isothiocyanates of the formula (X)

    R.sup.6 --N═C═L                                    (X)

in which

R⁶ and L have the abovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or

β) are reacted with carbamic acid chlorides or thiocarbamic acidchlorides of the formula (XI) ##STR24## in which L, R⁶ and R⁷ have theabovementioned meaning,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, and

(H)

that compounds of the formula (Ig) ##STR25## in which X, Y, D¹, D², Z,A, B and n have the abovementioned meaning,

and

E represents a metal ion equivalent (in particular an alkali metal oralkaline earth metal, such as lithium, sodium, potassium, magnesium orcalcium) or an ammonium ion,

are obtained when compounds of the formula (Ia) ##STR26## in which X, Y,Z, A, B, D¹, D² and n have the abovementioned meaning,

are reacted with metal compounds of the formula (XII) or amines of theformula (XIII) ##STR27## in which Me represents mono- or divalent metalions (as mentioned above for E) and

t represents the number 1 or 2 and

R⁹, R¹⁰ and R¹¹ independently of one another represent hydrogen, alkyl(preferably C₁ -C₈ -alkyl), alkoxy (preferably C₁ -C₈ -alkoxy) orhydroxyl,

if appropriate in the presence of a diluent.

It has furthermore been found that the novel 2-aryl-3-hydroxy-Δ²-cyclopentenone derivatives of the formula (I) are distinguished byoutstanding herbicidal, acaricidal and insecticidal actions.

Formula (I) provides a general definition of the compounds according tothe invention.

Preferred substituents and ranges of the radicals listed in the formulaementioned above and below are explained in the following.

X preferably represents halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulphinyl,C₁ -C₆ -alkylsulphonyl, C₁ -C₃ -halogenoalkyl or C₁ -C₃ -halogenoalkoxy.

Y preferably represents hydrogen, halogen, nitro, cyano, C₁ -C₆ -alkyl,C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulphinyl, C₁ -C₆ -alkylsulphonyl, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy.

Z preferably represents halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy or C₁ -C₃ -halogenoalkoxy.

n preferably represents 0, 1, 2 or 3,

or the radicals X and Z, together with the phenyl radical to which theyare bonded, preferably represent the naphthalene radical of the formula##STR28## in which Y has the abovementioned meaning.

A and B independently of one another preferably represent C₁ -C₁₂-alkyl, C₃ -C₈ -alkenyl, C₃ -C₈ -alkinyl, C₁ -C₁₀ -alkoxy-C₁ -C₈ -alkyl,poly-C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl or C₁ -C₁₀ -alkylthio-C₁ -C₈ -alkyl,in each case optionally substituted once or several times in anidentical or different manner by halogen, or saturated or unsaturatedcycloalkyl which has 3 to 8 ring atoms, is optionally substituted onceor several times in an identical or different manner by halogen, C₁ -C₆-alkyl or C₁ -C₆ -alkoxy and in which at least one methylene group isoptionally replaced by oxygen and/or sulphur, or phenyl or phenyl-C₁ -C₆-alkyl, in each case optionally substituted once or several times in anidentical or different manner by halogen, C₁ -C₆ -allyl, C₁ -C₆-halogenoalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkoxy, cyano or nitro,

or

A and B, together with the carbon atom to which they are bonded,preferably form a saturated or unsaturated 3- to 8-membered ring whichoptionally contains oxygen and/or sulphur and is optionally substitutedonce or several times in an identical or different manner by halogen, C₁-C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenalkoxy, C₁ -C₄ -alkylthio or phenyl which is optionally substituted byhalogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy, or

A and B, together with the carbon atom to which they are bonded,preferably represent C₃ -C₈ -cycloalkyl, in which two substituents,together with the carbon atoms to which they are bonded, represent asaturated or unsaturated 5- to 7-membered ring which is optionallysubstituted once or several times in an identical or different manner byhalogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy and can contain oxygen orsulphur.

D¹ and D² independently of one another preferably represent hydrogen,halogen or C₁ -C₆ -alkyl which is optionally substituted once or severaltimes in an identical or different manner by halogen, or representphenyl which is optionally substituted once or several times in anidentical or different manner by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy,nitro, C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy.

G preferably represents hydrogen (a), or represents one of the groups##STR29## in which E represents a metal ion equivalent or an ammoniumion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ preferably represents C₁ -C₂₀ -alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈-alkoxy-C₁ C₈ -alkyl, C₁ -C₈ -alkylthio-C₁ -C₈ -alkyl or poly-C₁ -C₈-alkoxy-C₂ -C₈ -alkyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, orsaturated or unsaturated cycloalkyl having 3 to 8 ring atoms, which isoptionally substituted once or several times in an identical ordifferent manner by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy and inwhich at least one methylene group can be replaced by an oxygen and/orsulphur atom,

or represents phenyl which is optionally substituted once or severaltimes in an identical or different manner by halogen, nitro, cyano, C₁-C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆-halogenoalkoxy,

or represents phenyl-C₁ -C₆ -alkyl which is optionally substituted onceor several times in an identical or different manner by halogen, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy,

or represents hetaryl which has 5 or 6 ring atoms and is optionallysubstituted once or several times in an identical or different manner byhalogen or C₁ -C₆ -alkyl,

or represents phenoxy-C₁ -C₆ -alkyl which is optionally substituted onceor several times in an identical or different manner by halogen or C₁-C₆ -alkyl,

or represents hetaryloxy-C₁ -C₆ -alkyl which has 5 or 6 ring atoms andis optionally substituted once or several times in an identical ordifferent manner by halogen, amino or C₁ -C₆ -alkyl.

R² preferably represents C₁ -C₂₀ -alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈-alkoxy-C₂ -C₈ -alkyl or poly-C₁ -C₈ -alkoxy-C₂ -C₈ -alkyl, in each caseoptionally substituted once or several times in an identical ordifferent manner by halogen, or represents C₃ -C₈ -cycloalkyl which isoptionally substituted once or several times in an identical ordifferent manner by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy,

or represents phenyl or benzyl, in each case optionally substituted onceor several times in an identical or different manner by halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₆ -halogenoalkyl.

R³ preferably represents C₁ -C₁₂ -alkyl in each case optionallysubstituted once or several times in an identical or different manner byhalogen, or represents phenyl or phenyl-C₁ -C₄ -alkyl, in each caseoptionally substituted once or several times in an identical ordifferent manner by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₃-halogenoalkyl, C₁ -C₃ -halogenoalkoxy, cyano or nitro

R⁴ and R⁵ independently of one another preferably represent C₁ -C₈-alkyl, C₁ -C₈ -alkoxy, C₁ -C₈ -alkylamino, C₃ -C₈ -alkenylamino, di-(C₁-C₈ -alkyl)-amino, di-(C₃ -C₈ -alkenyl)-amino, C₁ -C₈ -alkylthio, C₃ -C₅-alkenylthio, C₃ -C₅ -alkinylthio or C₃ -C₇ -cycloalkylthio, in eachcase optionally substituted once or several times in an identical ordifferent manner by halogen, or represent phenyl, phenoxy or phenylthio,in each case optionally substituted once or several times in anidentical or different manner by halogen, nitro, cyano, C₁ -C₄ -alkoxy,C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halogenoalkylthio, C₁-C₄ -alkyl or C₁ -C₄ -halogenoalkyl.

R⁶ and R⁷ independently of one another preferably represent hydrogen, orrepresent C₁ -C₁₀ -alkyl, C₁ -C₁₀ -alkoxy, C₃ -C₈ -alkenyl or C₁ -C₁₀-alkoxy-C₁ -C₁₀ -alkyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, orrepresent phenyl which is optionally substituted once or several timesin an identical or different manner by halogen, C₁ -C₃ -halogenoalkyl,C₁ -C₈ -alkyl or C₁ -C₈ -alkoxy, or represent benzyl which is optionallysubstituted once or several times in an identical or different manner byhalogen, C₁ -C₈ -alkyl, C₁ -C₈ -halogenoalkyl or C₁ -C₈ -alkoxy, ortogether represent a C₂ -C₆ -alkylene radical, in which a methylenegroup can be replaced by oxygen or sulphur.

X particularly preferably represents fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -halogenoalkyl or C₁ -C₂-halogenoalkoxy.

Y particularly preferably represents hydrogen, fluorine, chlorine,bromine, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₂-halogenoallyl or C₁ -C₂ -halogenoalkoxy.

Z particularly preferably represents fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₂ -halogenoalkoxy.

n particularly preferably represents 0, 1 or 2.

A and B independently of one another particularly preferably representC₁ -C₁₀ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₈ -alkoxy-C₁ -C₆-alkyl, poly-C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₈ -alkylthio-C₁ -C₆-alkyl, in each case optionally substituted once to five times in anidentical or different manner by fluorine or chlorine, or saturated orunsaturated cycloalkyl which has 3 to 7 ring atoms, is optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, and in which one ortwo methylene groups are optionally replaced by oxygen and/or sulphuratoms, or phenyl or phenyl-C₁ -C₄ -alkyl, in each case optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁-C₄ -alkoxy, cyano or nitro,

or

A and B, together with the carbon atom to which they are bonded,particularly preferably form a saturated or unsaturated 3 to 7-memberedring which optionally contains oxygen and/or sulphur and is optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, C₁ -C₅ -alkyl, C₁ -C₅ -alkoxy, C₁ -C₃-halogenoalkyl, C₁ -C₄ -halogenoalkoxy, C₁ -C₃ -alkylthio or phenylwhich is optionally substituted once or several times in an identical ordifferent manner by fluorine, chlorine, bromine, C₁ -C₄ -alkyl or C₁ -C₄-alkoxy, or

A and B, together with the carbon atom to which they are bonded,particularly preferably represent C₄ -C₇ -cycloalkyl,

in which two substituents, together with the carbon atoms to which theyare bonded, represent a saturated or unsaturated 5- or 6-membered ringwhich is optionally substituted once to three times in an identical ordifferent manner by fluorine, chlorine, C₁ -C₃ -alkyl or C₁ -C₃ -alkoxyand can contain oxygen or sulphur.

D¹ and D² independently of one another particularly preferably representhydrogen, fluorine, chlorine or C₁ -C₄ -alkyl which is optionallysubstituted once to five times in an identical or different manner byfluorine or chlorine, or represent phenyl which is optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, nitro, C₁-C₂ -halogenoalkyl or C₁ -C₂ -halogenoalkoxy.

G particularly preferably represents hydrogen (a), or represents one ofthe groups ##STR30## in which E represents a metal ion equivalent or anammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ particularly preferably represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl,C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl or poly-C₁C₆ -alkoxy-C₂ -C₆ -alkyl, in each case optionally substituted once tonine times in an identical or different manner by halogen, or cycloalkylwhich has 3 to 7 ring atoms, and is optionally substituted once or sixtimes in an identical or different manner by fluorine, chlorine, C₁ -C₄-alkyl or C₁ -C₄ -alkoxy, and in which one or two methylene groups areoptionally replaced by oxygen and/or sulphur atoms,

or represents phenyl which is optionally substituted once to three timesin an identical or different manner by fluorine, chlorine, bromine,nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkyl or C₁-C₃ -halogenoalkoxy,

or represents phenyl-C₁ -C₄ -alkyl which is optionally substituted onceto three times in an identical or different manner by fluorine,chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃ -halogenoalkylor C₁ -C₃ -halogenoalkoxy,

or represents pyridyl, thienyl, furanyl, pyrimidyl, thiazolyl orpyrazolyl, in each case optionally substituted once or twice in anidentical or different manner by fluorine, chlorine or C₁ -C₆ -alkyl,

or represents phenoxy-C₁ -C₅ -alkyl which is optionally substituted onceto three times in an identical or different manner by fluorine,chlorine, bromine or C₁ -C₄ -alkyl,

or represents pyridyloxy-C₁ -C₅ -alkyl, pyrimidyloxy-C₁ -C₅ -alkyl orthiazolyloxy-C₁ -C₅ -alkyl, in each case optionally substituted once ortwice in an identical or different manner by fluorine, chlorine,bromine, amino or C₁ -C₄ -alkyl.

R² particularly preferably represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl,C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, ineach case optionally substituted once to nine times in an identical ordifferent manner by fluorine or chlorine, or represents C₃ -C₇-cycloalkyl which is optionally substituted once to five times in anidentical or different manner by fluorine, chlorine, C₁ -C₄ -alkyl or C₁-C₄ -alkoxy,

or represents phenyl or benzyl, in each case optionally substituted onceto three times in an identical or different manner by fluorine,chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃-halogenoalkyl.

R³ particularly preferably represents C₁ -C₈ -alkyl in each caseoptionally substituted once to five times in an identical or differentmanner by fluorine or chlorine, or represents phenyl or phenyl-C₁ -C₂-alkyl, in each case optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -halogenoalkoxy,cyano or nitro.

R⁴ and R⁵ independently of one another particularly preferably representC₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylamino, C₃ -C₆ -alkenylamino,di-(C₁ -C₆ -alkyl)-amino, di-(C₃ -C₆ -alkenyl)-amino, C₁ -C₆ -alkylthio,C₃ -C₄ -alkenylthio, C₃ -C₄ -alkinylthio or C₃ -C₆ -cycloalkylthio, ineach case optionally substituted once to five times in an identical ordifferent manner by fluorine or chlorine, or represent phenyl, phenoxyor phenylthio, in each case optionally substituted once to three timesin an identical or different manner by fluorine, chlorine, bromine,nitro, cyano, C₁ -C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio,C₁ -C₃ -halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃ -halogenoalkyl.

R⁶ and R⁷ independently of one another particularly preferably representhydrogen, or represent C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyl orC₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, in each case optionally substituted onceto five times in an identical or different manner by fluorine orchlorine, or represent phenyl which is optionally substituted once tothree times in an identical or different manner by fluorine, chlorine,C₁ -C₃ -halogenoalkyl, C₁ -C₃ -alkyl or C₁ -C₃ -alkoxy, or representbenzyl which is optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, C₁ -C₃ -alkyl, C₁-C₃ -halogenoalkyl or C₁ -C₃ -alkoxy, or together represent a C₄ -C₆-alkylene radical, in which a methylene group can be replaced by oxygenor sulphur.

X especially preferably represents fluorine, chlorine, bromine, nitro,cyano, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy orchlorodifluoromethoxy.

Y especially preferably represents hydrogen, fluorine, chlorine,bromine, nitro, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl,i-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy or chlorodifluoromethoxy.

Z especially preferably represents fluorine, chlorine, bromine, nitro,cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,methoxy, ethoxy, trifluoromethoxy, difluoromethoxy orchlorodifluoromethoxy.

n especially preferably represents 0 or 1.

A and B independently of one another especially preferably represent C₁-C₈ -alkyl, C₃ -C₄ -alkenyl, C₃ -C₄ -alkinyl, C₁ -C₆ -alkoxy-C₁ -C₄-alkyl, poly-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₆ -alkylthio-C₁ -C₄-alkyl, in each case optionally substituted once to three times in anidentical or different manner by fluorine or chlorine, or cycloalkylwhich has 3 to 6 ring atoms, is optionally substituted once or twice inan identical or different manner by fluorine, chlorine, methyl, ethyl,methoxy or ethoxy, and

in which one or two methylene groups are optionally replaced by oxygenand/or sulphur atoms, or phenyl or benzyl, in each case optionallysubstituted once or twice in an identical or different manner byfluorine, chlorine, methyl, ethyl, propyl, iso-propyl, methoxy, ethoxy,trifluoromethyl, cyano or nitro,

or

A and B, together with the carbon atom to which they are bonded,especially preferably form a saturated or unsaturated 3- to 6-memberedring which optionally contains oxygen and/or sulphur and is optionallysubstituted once or twice in an identical or different manner byfluorine, chlorine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, trifluoromethyl, C₁-C₂ -alkylthio or phenyl which is optionally substituted once or twicein an identical or different manner by fluorine, chlorine, methyl ormethoxy, or

A and B, together with the carbon atom to which they are bonded,especially preferably represent C₅ -C₆ -cycloalkyl, in which twosubstituents, together with the carbon atoms to which they are bonded,represent a saturated or unsaturated 5- or 6-membered ring which isoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, methyl, ethyl, methoxy or ethoxy and can containoxygen or sulphur.

D¹ and D² independently of one another especially preferably representhydrogen, fluorine, chlorine, methyl or ethyl, or represent phenyl whichis optionally substituted once or twice in an identical or differentmanner by fluorine, chlorine, methyl, methoxy or trifluoromethyl.

G especially preferably represents hydrogen (a), or represents one ofthe groups ##STR31## in which E represents a metal ion equivalent or anammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ especially preferably represents C₁ -C₁₄ -alkyl, C₂ -C₁₄ -alkenyl, C₁-C₄ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₆ -alkyl or poly-C₁-C₄ -alkoxy-C₂ -C₄ -alkyl, in each case optionally substituted once tothree times in an identical or different manner by fluorine or chlorine,or cycloalkyl which has 3 to 6 ring atoms, is optionally substitutedonce or twice in an identical or different manner by fluorine, chlorine,methyl, ethyl, methoxy or ethoxy, and in which one or two methylenegroups are optionally replaced by oxygen and/or sulphur atoms,

or represents phenyl which is optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, bromine, methyl,ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro,

or represents phenyl-C₁ -C₃ -alkyl, in particular benzyl which isoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl,methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

or represents pyridyl, thienyl or furanyl, in each case optionallysubstituted once or twice in an identical or different manner byfluorine, chlorine, methyl or ethyl,

or represents phenoxy-C₁ -C₄ -alkyl which is optionally substituted onceor twice in an identical or different manner by fluorine, chlorine,methyl or ethyl,

or represents pyridyloxy-C₁ -C₃ -alkyl, pyrimidyloxy-C₁ -C₃ -alkyl orthiazolyloxy-C₁ -C₃ -alkyl, in each case optionally substituted once ortwice in an identical or different manner by fluorine, chlorine, amino,methyl or ethyl.

R² especially preferably represents C₁ -C₁₄ -alkyl, C₂ -C₁₄ -alkenyl, C₁-C₄ -alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₄ -alkoxy-C₂ -C₆ -alkyl, in eachcase optionally substituted once to five times in an identical ordifferent manner by fluorine or chlorine, or represents C₃ -C₆-cycloalkyl which is optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, methyl, ethyl,methoxy or ethoxy,

or represents phenyl or benzyl, in each case optionally substituted onceor twice in an identical or different manner by fluorine, chlorine,nitro, cyano, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy ortrifluoromethyl.

R³ especially preferably represents C₁ -C₆ -alkyl which is optionallysubstituted once to three times in an identical or different manner byfluorine or chlorine, or represents phenyl or benzyl, in each caseoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro.

R⁴ and R⁵ independently of one another especially preferably representC₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylamino, C₃ -C₄ -alkenylamino,di-(C₁ -C₄ -alkyl)-amino, di-(C₃ -C₄ -alkenyl)-amino, C₁ -C₄ -alkylthio,in each case optionally substituted once to three times in an identicalor different manner by fluorine or chlorine, or represent phenyl,phenoxy or phenylthio, in each case optionally substituted once or twicein an identical or different manner by fluorine, chlorine, bromine,nitro, cyano, C₁ -C₂ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₂-chloroalkoxy, C₁ -C₂ -alkylthio, C₁ -C₂ -fluoroalkylthio, C₁ -C₂-chloroalkylthio or C₁ -C₃ -alkyl.

R⁶ and R⁷ independently of one another especially preferably representhydrogen, or represent C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄-alkoxy-C₁ -C₄ -alkyl, in each case optionally substituted once to threetimes in an identical or different manner by fluorine or chlorine, orrepresent phenyl which is optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, C₁ -C₂-halogenoalkyl, C₁ -C₂ -alkyl or C₁ -C₂ -alkoxy, or represent benzylwhich is optionally substituted once or twice in an identical ordifferent manner by fluorine, chlorine, bromine, C₁ -C₂ -alkyl, C₁ -C₂-halogenoalkyl or C₁ -C₂ -alkoxy, or together represent a C₄ -C₆-alkylene radical, in which a methylene group can be replaced by oxygenor sulphur.

The enantiomerically pure forms of compounds of the formula (I) areincluded in each case here.

A preferred group of compounds are compounds of the formula (Ih)##STR32## in which Y¹ has the meanings given above for Y in thedefinition of the compounds of the formula (I) with the exception ofhydrogen, and

A, B, D¹, D², X, Z and G have the meanings given above in the definitionof the compounds of the formula (I).

A particularly preferred group of compounds are those compounds of theformula (Ih) ##STR33## in which Y¹ has the abovementioned meaning,

A and B, together with the carbon atom to which they are bonded, form asaturated or unsaturated ring which is optionally interrupted by atleast one heteroatom and is optionally substituted, or

A and B, together with the carbon atom to which they are bonded, form aring in which two substituents, together with the carbon atoms to whichthey are bonded, form a saturated or unsaturated ring which isoptionally substituted once or several times in an identical ordifferent manner by halogen, alkyl or alkoxy and can contain oxygen orsulphur and

D¹, D², X, Z and G have the meanings given above in the definition ofthe compounds of the formula (I).

Another preferred group of compounds are the compounds of the formula(Ii) ##STR34## in which

Y¹ has the abovementioned meaning and

A, B, D¹, D², X and G have the meanings given above in the definition ofthe compounds of the formula (I).

Another particularly preferred group of compounds are those compounds ofthe formula (Ii) ##STR35## in which Y¹ has the abovementioned meaning,

A and B, together with the carbon atom to which they are bonded, form asaturated or unsaturated ring which is optionally interrupted by atleast one heteroatom and is optionally substituted, or

A and B, together with the carbon atom to which they are bonded, form aring in which two substituents, together with the carbon atoms to whichthey are bonded, form a saturated or unsaturated ring which isoptionally substituted once or several times in an identical ordifferent manner by halogen, alkyl or alkoxy and can contain oxygen orsulphur and

D¹, D², X and G have the meanings given above in the definition of thecompounds of the formula (I).

Another preferred group of compounds are compounds of the formula (Ij)##STR36## in which A, B, D¹, D², G, X and Z have the meanings givenabove in the definition of the compounds of the formula (I).

Another particularly preferred group of compounds are those compounds ofthe formula (Ij) ##STR37## in which A and B, together with the carbonatom to which they are bonded, form a saturated or unsaturated ringwhich is optionally interrupted by at least one heteroatom and isoptionally substituted, or

A and B, together with the carbon atom to which they are bonded, form aring in which two substituents, together with the carbon atoms to whichthey are bonded, form a saturated or unsaturated ring which isoptionally substituted once or several times in an identical ordifferent manner by halogen, alkyl or alkoxy and can contain oxygen orsulphur and

D¹, D², X, Z and G have the meanings given above in the definition ofthe compounds of the formula (I).

The abovementioned definitions of radicals and explanations givengenerally or in preferred ranges can be combined as desired with oneanother, that is to say also between the particular ranges and preferredranges. They apply to the end products and, correspondingly, to theprecursors and intermediates.

The compounds of the formula (I) which are preferred according to theinvention are those in which a combination of the meanings given aboveas preferred (preferably) is present.

The compounds of the formula (I) which are particularly preferredaccording to the invention are those in which a combination of themeanings given above as particularly preferred is present.

The compounds of the formula (I) which are especially preferredaccording to the invention are those in which a combination of themeanings given above as especially preferred is present.

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Ia) may be mentioned specifically: ##STR38##

                  TABLE 1                                                         ______________________________________                                        A              B         X       Y     Z.sub.n                                ______________________________________                                        CH.sub.3      CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                             C.sub.2 H.sub.5                                                                             CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                             CH(CH.sub.3).sub.2                                                                          CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                             CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                                           CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                              ##STR39##    CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                              ##STR40##    CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                             C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.5                                                                          CH.sub.3                                                                              CH.sub.3                                                                            6-CH.sub.3                             (CH.sub.2).sub.2     CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.4     CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.5     CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.6     CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.7     CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               CH.sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                               CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               CH(CH.sub.3)(CH.sub.2).sub.4                                                                       CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                ##STR41##           CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                ##STR42##           CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                ##STR43##           CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                ##STR44##           CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               CH.sub.2 CHCH.sub.3 CHCH.sub.3 (CH.sub.2).sub.2                                                    CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                               CH.sub.3      CH.sub.3   Cl      Cl    H                                      C.sub.2 H.sub.5                                                                             CH.sub.3   Cl      Cl    H                                      CH(CH.sub.3).sub.2                                                                          CH.sub.3   Cl      Cl    H                                      CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   Cl      Cl    H                                      (CH.sub.2).sub.4     Cl      Cl      H                                        (CH.sub.2).sub.5     Cl      Cl      H                                        (CH.sub.2).sub.6     Cl      Cl      H                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              Cl      Cl      H                                        (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      Cl      Cl      H                                         ##STR45##           Cl      Cl      H                                         ##STR46##           Cl      Cl      H                                        CH.sub.2 CHCH.sub.3 CHCH.sub.3 (CH.sub.2).sub.2                                                    Cl      Cl      H                                        (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      Cl      Cl      H                                        (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               Cl      Cl      H                                        CH.sub.3      CH.sub.3   Cl      H     6-Cl                                   C.sub.2 H.sub.5                                                                             CH.sub.3   Cl      H     6-Cl                                   CH(CH.sub.3).sub.2                                                                          CH.sub.3   Cl      H     6-Cl                                   CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   Cl      H     6-Cl                                   (CH.sub.2).sub.4     Cl      H       6-Cl                                     (CH.sub.2).sub.5     Cl      H       6-Cl                                     (CH.sub.2).sub.6     Cl      H       6-Cl                                     CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              Cl      H       6-Cl                                     (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      Cl      H       6-Cl                                      ##STR47##           Cl      H       6-Cl                                      ##STR48##           Cl      H       6-Cl                                     (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      Cl      H       6-Cl                                     (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               Cl      H       6-Cl                                     CH.sub.3      CH.sub.3   Cl      H     6-F                                    C.sub.2 H.sub.5                                                                             CH.sub.3   Cl      H     6-F                                    CH(CH.sub.3).sub.2                                                                          CH.sub.3   Cl      H     6-F                                    CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   Cl      H     6-F                                    (CH.sub.2).sub.4     Cl      H       6-F                                      (CH.sub.2).sub.5     Cl      H       6-F                                      (CH.sub.2).sub.6     Cl      H       6-F                                      CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              Cl      H       6-F                                      (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      Cl      H       6-F                                       ##STR49##           Cl      H       6-F                                       ##STR50##           Cl      H       6-F                                      (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      Cl      H       6-F                                      (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               Cl      H       6-F                                      CH.sub.3      CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H                                      C.sub.2 H.sub.5                                                                             CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H                                      CH(CH.sub.3).sub.2                                                                          CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H                                      CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                            H                                      (CH.sub.2).sub.4     CH.sub.3                                                                              CH.sub.3                                                                              H                                        (CH.sub.2).sub.5     CH.sub.3                                                                              CH.sub.3                                                                              H                                        (CH.sub.2).sub.6     CH.sub.3                                                                              CH.sub.3                                                                              H                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              CH.sub.3                                                                              CH.sub.3                                                                              H                                        (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      CH.sub.3                                                                              CH.sub.3                                                                              H                                         ##STR51##           CH.sub.3                                                                              CH.sub.3                                                                              H                                         ##STR52##           CH.sub.3                                                                              CH.sub.3                                                                              H                                        CH.sub.2 CHCH.sub.3 CHCH.sub.3 (CH.sub.2).sub.2                                                    CH.sub.3                                                                              CH.sub.3                                                                              H                                        (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      CH.sub.3                                                                              CH.sub.3                                                                              H                                        (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               CH.sub.3                                                                              CH.sub.3                                                                              H                                        CH.sub.3      CH.sub.3   Cl      CF.sub.3                                                                            6-Cl                                   C.sub.2 H.sub.5                                                                             CH.sub.3   Cl      CF.sub.3                                                                            6-Cl                                   CH(CH.sub.3).sub.2                                                                          CH.sub.3   Cl      CF.sub.3                                                                            6-Cl                                   CH.sub.2 CH(CH.sub.3).sub.2                                                                 CH.sub.3   Cl      CF.sub.3                                                                            6-Cl                                   (CH.sub.2).sub.4     Cl      CF.sub.3                                                                              6-Cl                                     (CH.sub.2).sub.5     Cl      CF.sub.3                                                                              6-Cl                                     (CH.sub.2).sub.6     Cl      CF.sub.3                                                                              6-Cl                                     CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                              Cl      CF.sub.3                                                                              6-Cl                                     (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                      Cl      CF.sub.3                                                                              6-Cl                                      ##STR53##           Cl      CF.sub.3                                                                              6-Cl                                      ##STR54##           Cl      CF.sub.3                                                                              6-Cl                                     (CH.sub.2).sub.2 CHOCH.sub.3 (CH.sub.2).sub.2                                                      Cl      CF.sub.3                                                                              6-Cl                                     (CH.sub.2).sub.2 CHOC.sub.2 H.sub.5 (CH.sub.2).sub.2                                               Cl      CF.sub.3                                                                              6-Cl                                     ______________________________________                                    

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Ib) may be mentioned specifically (Table 2):

                                      TABLE 2                                     __________________________________________________________________________     ##STR55##                                                                    A       B       X   Y   Z.sub.n                                                                           R.sup.1                                           __________________________________________________________________________    CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR56##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR57##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(.sub.2 CH.sub.2 OCH.sub.3             CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR58##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR59##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR60##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR61##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR62##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR63##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR64##                                        CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR65##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR66##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR67##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR68##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR69##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR70##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR71##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR72##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR73##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR74##                                        CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR75##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR76##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR77##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR78##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR79##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR80##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR81##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR82##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR83##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR84##                                        (CH.sub.2).sub.4                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR85##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR86##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR87##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR88##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR89##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR90##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR91##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR92##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR93##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR94##                                        (CH.sub.2).sub.5                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR95##                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR96##                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR97##                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR98##                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR99##                                        CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR100##                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR101##                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR102##                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR103##                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR104##                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                         CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR105##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR106##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR107##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR108##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR109##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR110##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR111##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR112##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR113##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR114##                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR115##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.3                                          (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.2 H.sub.5                                   (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.3 H.sub.7                                   (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C.sub.4 H.sub.9                                   (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH(CH.sub.3).sub.2                                (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 CH(CH.sub.3).sub.2                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.3                                 (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 C.sub.2 H.sub.5                 (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH(CH.sub.3).sub.2              (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CH.sub.2 C(CH.sub.3).sub.3                        (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR116##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 Cl                     (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR117##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3              (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        C(CH.sub.3)(CH.sub.2 OCH.sub.3).sub.2             (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        CHC(CH.sub.3).sub.2                               (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR118##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR119##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR120##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR121##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR122##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR123##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR124##                                       (CH.sub.2).sub.2 CH(OCH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         ##STR125##                                       __________________________________________________________________________

TABLE 3

Table 3 contains the compounds of the formula (Ib) in which A, B and R¹have the meanings given in Table 2 and X and Y in each case representchlorine and Z_(n) represents hydrogen.

TABLE 4

Table 4 contains the compounds of the formula (Ib) in which A, B and R¹have the meanings given in Table 2 and X and Y in each case representCH₃ and Z_(n) represents hydrogen.

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Ic) may be mentioned specifically (Table 5): ##STR126##

                                      TABLE 5                                     __________________________________________________________________________    A      B       X   Y   Z.sub.n                                                                           L M R.sup.2                                        __________________________________________________________________________    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                                      CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                        ##STR127##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.3                                       CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                 ##STR128##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                 ##STR129##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O C.sub.2 H.sub.5                                CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                              ##STR130##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                              ##STR131##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3).sub.2                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                     ##STR132##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                     ##STR133##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 CH(CH.sub.3).sub.2                    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                     ##STR134##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                     ##STR135##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH(CH.sub.3)C.sub.2 H.sub.5                    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                      ##STR136##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                      ##STR137##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O CH.sub.2 C(CH.sub.3).sub.3                     CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR138##                                    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR139##                                    CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR140##                                    (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR141##                                    (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR142##                                    (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR143##                                    CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR144##                                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR145##                                     ##STR146##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR147##                                     ##STR148##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR149##                                    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR150##                                    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR151##                                    CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR152##                                    (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR153##                                    (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR154##                                    (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR155##                                    CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR156##                                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR157##                                     ##STR158##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR159##                                     ##STR160##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR161##                                    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR162##                                    C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR163##                                    CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR164##                                    (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR165##                                    (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR166##                                    (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR167##                                    CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR168##                                    (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR169##                                     ##STR170##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR171##                                     ##STR172##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O O                                                                                ##STR173##                                    CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                 ##STR174##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                 ##STR175##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S C.sub.2 H.sub.5                                CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             C.sub.2 H.sub.5                                                                      CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             CF.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             (CH.sub.2).sub.4                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             (CH.sub.2).sub.6                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.3                                                        CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             (CH.sub.2).sub.2 CH(CH.sub.3)(CH.sub.2).sub.2                                                CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                              ##STR176##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                              ##STR177##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O S CH(CH.sub.3).sub.2                             __________________________________________________________________________

TABLE 6

Table 6 contains the compounds of the formula (Ic) in which A, B, L, Mand R² have the meanings given in Table 5 and X and Y in each caserepresent chlorine and Z_(n) represents hydrogen.

TABLE 7

Table 7 contains the compounds of the formula (Ic) in which A, B, L, Mand R² have the meanings given in Table 5 and X and Y in each caserepresent CH₃ and Z_(n) represents hydrogen.

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Id) may be mentioned specifically:

                  TABLE 8                                                         ______________________________________                                         ##STR178##                                                                   A     B       X       Y     Z.sub.n                                                                              R.sup.3                                    ______________________________________                                        (CH.sub.2).sub.5                                                                        CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                                                            ##STR179##                                  (CH.sub.2).sub.5                                                                        CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                                                            ##STR180##                                  (CH.sub.2).sub.5                                                                        CH.sub.3                                                                              CH.sub.3                                                                              6-CH.sub.3                                                                           CH.sub.3                                     ______________________________________                                    

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Ie) may be mentioned specifically:

                                      TABLE 9                                     __________________________________________________________________________     ##STR181##                                                                   A  B   X   Y   Z.sub.n                                                                            L  R.sup.4                                                                              R.sup.5                                         __________________________________________________________________________    (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         S  CF.sub.3 CH.sub.2 O                                                                  CH.sub.3                                        (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  CH.sub.3O                                                                            C.sub.2 H.sub.5S                                (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  CH.sub.3O                                                                            (CH.sub.3).sub.2 CHS                            (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  CH.sub.3O                                                                             ##STR182##                                     (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  C.sub.2 H.sub.5 O                                                                    C.sub.2 H.sub.5S                                (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  C.sub.2 H.sub.5 O                                                                    (CH.sub.3).sub.2 CHS                            (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                         O  C.sub.2 H.sub.5 O                                                                     ##STR183##                                     __________________________________________________________________________

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(If) may be mentioned specifically (Table 10):

                                      TABLE 10                                    __________________________________________________________________________     ##STR184##                                                                   A  B   X   Y   Z.sub.n                                                                           L  R.sup.6 R.sup.7                                         __________________________________________________________________________    (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O  CH.sub.3                                                                              CH.sub.3                                        (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        S  CH.sub.3                                                                              CH.sub.3                                        (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O  CH.sub.2CHCH.sub.2                                                                    CH.sub.2CHCH.sub.2                              (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O  (CH.sub.2).sub.2O(CH.sub.2).sub.2                       (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O  (CH.sub.2).sub.5                                        (CH.sub.2).sub.5                                                                     CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        O                                                                                 ##STR185##                                                                           C.sub.2 H.sub.5                                 __________________________________________________________________________

In addition to the compounds mentioned in the preparation examples, thefollowing 2-aryl-3-hydroxy-Δ² -cyclopentenone derivatives of the formula(Ig) may be mentioned specifically (Table 11):

                                      TABLE 11                                    __________________________________________________________________________     ##STR186##                                                                   A         B      X    Y    Z.sub.n                                                                            E                                             __________________________________________________________________________    CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         NH.sub.4                                      CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            C.sub.2 H.sub.5                                                                         CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            CF.sub.3  CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            (CH.sub.2).sub.4 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            (CH.sub.2).sub.5 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            (CH.sub.2).sub.6 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            CH.sub.2CH(CH.sub.3)(CH.sub.2).sub.3                                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            (CH.sub.2).sub.2CH(CH.sub.3)(CH.sub.2).sub.2                                                   CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                             ##STR187##      CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                             ##STR188##      CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         Na                                            CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    C.sub.2 H.sub.5                                                                         CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    CH(CH.sub.3).sub.2                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    CF.sub.3  CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    (CH.sub.2).sub.4 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    (CH.sub.2).sub.5 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    (CH.sub.2).sub.6 CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    CH.sub.2CH(CH.sub.3)(CH.sub.2).sub.3                                                           CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    (CH.sub.2).sub.2CH(CH.sub.3)(CH.sub.2).sub.2                                                   CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                     ##STR189##      CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                     ##STR190##      CH.sub.3                                                                           CH.sub.3                                                                           6-CH.sub.3                                                                         i-C.sub.3 H.sub.7 NH.sub.3                    __________________________________________________________________________

TABLE 12

Table 12 contains the compounds of the formula (Ig) in which A, B and Ehave the meanings given in Table 11 and X and Y in each case representchlorine and Z_(n) represents hydrogen

TABLE 13

Table 13 contains the compounds of the formula (Ig) in which A, B and Ehave the meanings given in Table 11 and X and Y in each case representCH₃ and Z_(n) represents hydrogen.

If ethyl 5-(2,6-dichlorophenyl)-2,2-dimethyl-4-oxo-valerate is usedaccording to process (A), the course of the process according to theinvention can be represented by the following equation: ##STR191##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-dimethyl-Δ² -cyclopentenoneand pivaloyl chloride are used as starting material according to process(B) (version α), the course of the process according to the inventioncan be represented by the following equation: ##STR192##

If 2-(2,4-dimethylphenyl)-3-hydroxy-4-methyl-4-phenyl-Δ² -cyclopentenoneand acetic anhydride are used as starting compounds according to process(B) (version B), the course of the process according to the inventioncan be represented by the following equation: ##STR193##

If 2-(2,4-dichlorophenyl)-3-hydroxy-4-isopropyl-4-methyl-Δ²-cyclopentenone and ethoxyethyl chloroformate are used as startingcompounds according to process (C), the course of the process accordingto the invention can be represented by the following equation:##STR194##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4-ethyl-4-methyl-Δ²-cyclopentenone and methyl chloromonothioformate are used as startingsubstances according to process (D.sub.α), the course of the reactioncan be represented as follows: ##STR195##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-pentamethylene-Δ²-cyclopentenone, carbon disulphide and methyl iodide are used asstarting components according to process (D.sub.β), the course of thereaction can be represented as follows: ##STR196##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-(3-methoxy)-pentamethylene-Δ²-cyclopentenone and methanesulphonyl chloride are used as startingsubstance according to process (E), the course of the reaction can berepresented by the following equation: ##STR197##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-dimethyl-Δ² -cyclopentenoneand methanethio-phosphonic acid chloride-(2,2,2-trifluoroethyl ester)are used as starting substances according to process (F), the course ofthe reaction can be represented by the following equation: ##STR198##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-tetramethylene-Δ²-cyclopentenone and ethyl isocyanate are used as starting substancesaccording to process (G.sub.α), the course of the reaction can berepresented by the following equation: ##STR199##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4-trifluoromethyl-4-methyl Δ²-cyclopentenone and dimethylcarbamoyl chloride are used as startingsubstances according to process (G.sub.β), the course of the reactioncan be represented by the following scheme: ##STR200##

If 2-(2,4,6-trimethylphenyl)-3-hydroxy-4,4-dimethyl-Δ² -cyclopentenoneand NaOH are used as components according to process (H), the course ofthe process according to the invention can be represented by thefollowing equation: ##STR201##

The compounds of the formula (II) ##STR202## in which A, B, D¹, D², X,Y, Z, n and R⁸ have the abovementioned meaning,

required as starting substances in the above process (A) are novel.

They can be prepared by methods which are known in principle.

The 5-aryl-4-ketocarboxylic acid esters of the formula (II) areobtained, for example, when 5-aryl-4-ketocarboxylic acids of the formula(XIV) ##STR203## in which X, Y, Z, A, B, D¹, D² and n have theabovementioned meaning,

are esterified (cf. for example, Organikum, 15th Edition, Berlin, 1977,page 499).

The 5-aryl-4-ketocarboxylic acids of the formula (XIV) ##STR204## inwhich A, B, D¹, D², X, Y, Z and n have the abovementioned meaning,

are novel, but can be prepared by methods which are known in principle.

The 5-aryl-4-ketocarboxylic acids of the formula (XIV) are obtained, forexample, when carboxylic acid anhydrides of the formula (XV) ##STR205##in which A, B, D¹ and D² have the abovementioned meaning,

are reacted with organometallic compounds of the formula (XVI)##STR206## in which X, Y, Z and n have the abovementioned meaning,

Me represents mono- or divalent metal ions, for example of lithium ormagnesium,

Hal represents chlorine or bromine

and

l represents a number 0 or 1

in the presence of a diluent (cf., for example, Organikum, 15th Edition,Berlin, 1977, Page 623).

The compounds (XV) and (XVI) are known in some cases and/or can beprepared in a simple manner by known processes (cf., for example,Organikum, 15th Edition, Berlin, 1977, pages 525, 526 and 623).

5-Aryl-4-ketocarboxylic acids of the formula (XIV) ##STR207## in whichA, B, D¹, D², X, Y, Z and n have the abovementioned meaning,

furthermore are obtained when 2-phenyl-3-oxo-adipic acid esters of theformula (XVII) ##STR208## in which A, B, D¹, D², X, Y, Z and n have theabovementioned meaning and

R⁸ and R^(8') represent alkyl (in particular C₁ -C₈ -alkyl),

are decarboxylated, if appropriate in the presence of a diluent and ifappropriate in the presence of a base or acid (cf., for example,Organikum, 15th Edition, Berlin, 1977, page 519 to 521).

The compounds of the formula (XVII) ##STR209## in which A, B, D¹, D², X,Y, Z, R⁸, R^(8') and n have the abovementioned meaning,

are novel.

The compounds of the formula (XVII) are obtained, for example, whendicarboxylic acid half-ester chlorides of the formula (XVIII),##STR210## in which A, B, D¹, D² and R⁸ have the abovementioned meaningand

Hal represents chlorine or bromine,

are acylated with a phenylacetic acid ester of the formula (XIX)##STR211## in which X,Y, Z, R^(8') and n have the abovementionedmeaning,

in the presence of a diluent and in the presence of a base (cf., forexample, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc.Chem. Commun., (1987), 1228).

The compounds of the formulae (XVIII) and (XIX) are generally knowncompounds of Organic Chemistry and/or can be prepared in a simple mannerby methods known in principle.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D¹, D², X, Y, Z, n and R⁸ have the abovementioned meaningare subjected to an intramolecular condensation reaction in the presenceof bases.

Diluents which can be employed in process (A) according to the inventionare all the organic solvents which are inert towards the reactionparticipants. Solvents which can preferably be used are hydrocarbons,such as toluene and xylene, and furthermore ethers, such as dibutylether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycoldimethyl ether, and furthermore polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone.Alcohols, such as methanol, ethanol, propanol, iso-propanol, butanol,isobutanol, tert-butanol, can moreover be employed.

Bases (deprotonating agents) which can be employed in carrying outprocess (A) according to the invention are all the customary protonacceptors. Proton acceptors which can preferably be used as alkali metaland alkaline earth metal oxides, hydroxides and carbonates, such assodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide,sodium carbonate, potassium carbonate and calcium carbonate, which canalso be employed in the presence of phase transfer catalysts, such as,for example, triethylbenzylammonium chloride, tetrabutyl-ammoniumbromide, Adogen 464 (methyltrialkyl(C₈ -C₁₀)ammonium chloride) or TDA 1(tris-(methoxyethoxyethyl)-amine). Alkali metals, such as sodium orpotassium, can moreover be used. It is furthermore possible to employalkali metal and alkaline earth metal amides and hydrides, such assodium amide, sodium hydride and calcium hydride, and in addition alsoalkali metal alcoholates, such as sodium methylate, sodium ethylate andpotassium tert-butylate.

The reaction temperatures can be varied within a substantial range incarrying out process (A) according to the invention. The reaction is ingeneral carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

Process (A) according to the invention is in general carried out undernormal pressure.

In carrying out process (A) according to the invention, the reactioncomponents of the formula (II) and the deprotonating bases are ingeneral employed in approximately equimolar amounts. However, it is alsopossible to use one or other of the components in a relatively largeexcess (up to 3 mol).

Process (Bα) is characterized in that compounds of the formula (Ia) arereacted with carboxylic acid halides of the formula (III).

Diluents which can be employed in process (Bα) according to theinvention are all the solvents which are inert towards the acid halides.Solvents which can preferably be used are hydrocarbons, such as benzine,benzene, toluene, xylene and tetralin, and furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbonatedtetrachloride, chlorobenzene and o-dichlorobenzene, and in additionketones, such as acetone and methyl isopropyl ketone, and furthermoreethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuranand dioxane, and additionally carboxylic acid esters, such as ethylacetate, and also strongly polar solvents, such as dimethyl sulphoxideand sulpholane. If the stability of the acid halide to hydrolysisallows, the reaction can also be carried out in the presence of water.

Possible acid-binding agents in the reaction by process (Bα) accordingto the invention are all the customary acid acceptors. Acid acceptorswhich can preferably be used are tertiary amines, such as triethylamine,pyridine, diazabiyclooctane (DABCO), diazabicycloundecane (DBU),diazabicyclononene (DBN), Hunig base and N,N-dimethyl aniline, andfurthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, and additionally alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate.

The reaction temperatures can be varied within a substantial range inprocess (Bα) according to the invention. The reaction is in generalcarried out at temperatures between -20° C. and +150° C., preferablybetween 0° C. and 100° C.

In carrying out process (Bα) according to the invention, the startingsubstances of the formula (Ia) and the carboxylic acid halide of theformula (III) are in general used in approximately equivalent amounts.However, it is also possible to employ the carboxylic acid halide in arelatively large excess (up to 5 mol). Working up is carried out bycustomary methods.

Process (Bβ) is characterized in that compounds of the formula (Ia) arereacted with carboxylic acid anhydrides of the formula (IV).

Diluents which can be used in process (Bβ) according to the inventionare preferably those diluents which are also preferably possible whenacid halides are used. In addition, a carboxylic acid anhydride employedin excess can also simultaneously function as the diluent.

The reaction temperatures can be varied within a substantial range inprocess (Bβ) according to the invention. The reaction is in generalcarried out at temperatures between -20° C. and +150° C., preferablybetween 0° C. and 100° C.

In carrying out the process according to the invention, the startingsubstances of the formula (Ia) and the carboxylic acid anhydride of theformula (IV) are in general used in approximately equivalent amounts.However, it is also possible to employ the carboxylic acid anhydride ina relatively large excess (up to 5 mol). Working up is carried out bycustomary methods.

In general, a procedure is followed in which the diluent and thecarboxylic acid anhydride present in excess, as well as the carboxylicacid formed, are removed by distillation or by washing with an organicsolvent or with water.

Process (C) is characterized in that compounds of the formula (Ia) arereacted with chloroformic acid esters or chloroformic acid thiol estersof the formula (V).

Possible acid-binding agents in the reaction by process (C) according tothe invention are all the customary acid acceptors. Acid acceptors whichcan preferably be used are tertiary amines, such as triethylamine,pyridine, DABCO, DBN, DBU, Hunig base and N,N-dimethyl aniline, andfurthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, and in addition alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate.

Diluents which can be employed in process (C) according to the inventionare all the solvents which are inert towards the chloroformic acidesters or chloroformic acid thiol esters. Solvents which can preferablybe used are hydrocarbons, such as benzine, benzene, toluene, xylene andtetralin, and furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, and in addition ketones, such as acetone and methylisopropyl ketone, and moreover ethers, such as diethyl ether,tetrahydrofuran and dioxane, and additionally carboxylic acid esters,such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

The reaction temperatures can be varied within a substantial range incarrying out process (C) according to the invention. If the reaction iscarried out in the presence of a diluent and an acid-binding agent, thereaction temperatures are in general between -20° C. and +100° C.,preferably between 0° C. and 50° C.

Process (C) according to the invention is in general carried out undernormal pressure.

In carrying out process (C) according to the invention, the startingsubstances of the formula (Ia) and the corresponding chloroformic acidesters or chloroformic acid thiol esters of the formula (V) are ingeneral used in approximately equivalent amounts. However, it is alsopossible to employ one or other of the components in a relatively largeexcess (up to 2 mol). Working up is then carried out by customarymethods. In general, a procedure is followed in which salts which haveprecipitated out are removed and the reaction mixture which remains isconcentrated by stripping off the diluent.

In preparation process (Dα), about 1 mol of chloromonothioformic acidester or chlorodithioformic acid ester of the formula (VI) is reactedper mol of starting compound of the formula (Ia) at 0° to 120° C.,preferably at 20° to 60° C.

Possible diluents which are optionally added are all the inert polarorganic solvents, such as halogenohydrocarbons, nitrites, carboxylicacid esters, ethers, amides, sulphones and sulphoxides.

Acetonitrile, ethyl acetate, dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound of theformula (Ia) is prepared by addition of strong deprotonating agents,such as, for example, sodium hydride or potassium tert-butylate, furtheraddition of acid-binding agents can be omitted.

If acid-binding agents are employed, the customary inorganic or organicbases are possible, and sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine may be listed as examples.

The reaction can be carried out under normal pressure or under increasedpressure, and is preferably carried out under normal pressure. Workingup is carried out by customary methods.

In preparation process (Dβ), the equimolar amount or an excess of carbondisulphide is added per mol of starting compound of the formula (II).This reaction is preferably carried out at temperatures from 0° to 50°C. and in particular at 20° to 30° C.

If appropriate, process (Dβ) is carried out in the presence of a base.

Bases which can be employed in process (Dβ) are all the customary protonacceptors. Proton acceptors which can preferably be used are alkalimetal hydrides, alkali metal alcoholates, alkali metal or alkaline earthmetal carbonates or bicarbonates or nitrogen bases. Examples which maybe mentioned are sodium hydride, sodium methanolate, sodium hydroxide,calcium hydroxide, potassium carbonate, sodium bicarbonate,triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline,diazabicyclooctane (DABCO), diazabicyclononene (DBN) anddiazabicycloundecene (DBU).

Diluents which can be used in this process are all the customarysolvents.

Solvents which can preferably be used are aromatic hydrocarbons, such asbenzene or toluene, alcohols, such as methanol, ethanol, isopropanol orethylene glycol, nitrites, such as acetonitrile, ethers, such astetrahydrofuran or dioxane, amides, such as dimethylformamide, or otherpolar solvents, such as dimethyl sulphoxide or sulpholane. It is oftenexpedient first to prepare the corresponding salt from the compound ofthe formula (Ia) by addition of a deprotonating agent (such as, forexample, potassium tert-butylate or sodium hydride). The compound of theformula (Ia) is reacted with carbon disulphide until the formation ofthe intermediate compound has ended, for example after the mixture hasbeen stirred at room temperature for several hours.

The further reaction with the alkyl halide of the formula (VII) ispreferably carried out at 0° to 70° C., and in particular at 20° to 50°C. At least the equimolar amount of alkyl halide is employed for thisreaction.

The reaction is carried out under normal pressure or under increasedpressure, preferably under normal pressure.

Working up is again carried out by customary methods.

In preparation process (E), about 1 mol of sulphonic acid chloride ofthe formula (VIII) is reacted per mol of starting compound of theformula (Ia) at 0° to 150° C., preferably at 20° to 70° C.

Possible diluents which are optionally added are all the inert polarorganic solvents, such as halogenohydrocarbons, carboxylic acid esters,ethers, amides, nitriles, sulphones and sulphoxides.

Acetonitrile, ethyl acetate, dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound of theformula (Ia) is prepared by addition of strong deprotonating agents(such as, for example, sodium hydride or potassium tert-butylate),further addition of acid-binding agents can be omitted.

If acid-binding agents are employed, the customary inorganic or organicbases are possible, examples which may be mentioned being sodiumhydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine.

The reaction can be carried out under normal pressure or under increasedpressure, and is preferably carried out under normal pressure. Workingup is carried out by customary methods.

If appropriate, preparation process (E) can be carried out under phasetransfer conditions (W. J. Spillane et. al.; J. Chem. Soc., Perkin TransI, (3) 677-9 (1982)). In this case, 0.3 to 5 mol of sulphonic acidchloride of the formula (VIII), preferably 1 mol, are reacted per mol ofstarting compound of the formula Ia) at 0° to 150° C., preferably at 20°to 70° C.

Phase transfer catalysts which can be used are all the quaternaryammonium salts, preferably tetraoctylammonium bromide andbenzyltriethylammonium chloride.

Organic solvents which can be used in this case are all the non-polarinert solvents, and benzene and toluene are preferably employed.

In preparation process (F), 1 mol of the compound (Ia) and 1 to 2,preferably 1 to 1.3, mol of the phosphorus compound of the formula (IX)are reacted at temperatures between -40° C. and 150° C., preferablybetween -10 and 110° C., to give compounds of the formula (Ie).

Possible diluents which are optionally added are all the inert polarorganic solvents, such as halogenohydrocarbons, ethers, amides,nitrites, sulphides, sulphones, sulphoxides etc.

Acetonitrile, ethyl acetate, dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride are preferably employed.

Possible acid-binding agents which are optionally added are thecustomary inorganic or organic bases, such as hydroxides and carbonates.Examples which may be mentioned are sodium hydroxide, sodium carbonate,potassium carbonate, pyridine, triethylamine and DABCO.

The reaction can be carried out under normal pressure or under increasedpressure, and is preferably carried out under normal pressure. Workingup is carried out by customary methods of organic chemistry.Purification of the end products obtained is preferably carried out bycrystallization, chromatographic purification or by so-called "incipientdistillation", i.e. removal of the volatile constituents in vacuo.

In preparation process (Gα), about 1 mol of isocyanate or isothiocyanateof the formula (X) is reacted per mol of starting compound of theformula (Ia) at 0° to 100° C., preferably at 20° to 50° C.

Possible diluents which are optionally added are all the inert organicsolvents, such as hydrocarbons, halogenated hydrocarbons, carboxylicacid esters, ethers, amides, nitrites, sulphones and sulphoxides.Toluene, methylene chloride, tetrahydrofuran, ethyl acetate,dimethylformamide or dimethyl sulphoxide are preferably employed.

If appropriate, catalysts can be added to accelerate the reaction.Catalysts which can very advantageously be employed are organotincompounds, such as, for example, dibutyltin dilaurate. The reaction ispreferably carried out under normal pressure.

In preparation process (Gβ), about 1 mol of carbamic acid chloride orthiocarbamic acid chloride of the formula (XI) is reacted per mol ofstarting compound of the formula (Ia) at 0° to 150° C., preferably at20° to 70° C.

Possible diluents which are optionally added are all the inert polarorganic solvents, such as halogenohydrocarbons, carboxylic acid esters,ethers, amides, sulphones or sulphoxides.

Acetonitrile, ethyl acetate, dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compound of theformula (Ia) is prepared by addition of strong deprotonating agents(such as, for example, sodium hydride or potassium tert-butylate),further addition of acid-binding agents can be omitted.

If acid-binding agents are employed, the customary inorganic or organicbases are possible, examples which may be mentioned being sodiumhydroxide, sodium carbonate, potassium carbonate, pyridine,triethylamine and DABCO.

The reaction can be carried out under normal pressure or under increasedpressure, and is preferably carried out under normal pressure. Workingup is carried out by customary methods.

Process (H) is characterized in that compounds of the formula (Ia) arereacted with metal compounds of the formula (XII) or amines of theformula (XIII).

Diluents which can be employed in the process according to the inventionare preferably ethers, such as tetrahydrofuran, dioxane or diethylether, or alcohols, such as methanol, ethanol or isopropanol, or elsewater. Process (H) according to the invention is in general carried outunder normal pressure. The reaction temperatures are in general between-20° C. and 100° C., preferably between 0° C. and 50° C.

In carrying out process (H) according to the invention, the startingsubstances of the formula (Ia) and (XII) or (XIII) are in general usedin approximately equimolar amounts. However, it is also possible toemploy one or other of the components in a relatively large excess (upto 2 mol). In general, a procedure is followed in which the reactionmixture is concentrated by stripping off the diluent.

The following compounds of the formula (II) may be mentioned asexamples:

methyl 5-(2,4-dichlorophenyl)-4-oxo-2,2-dimethyl-pentanecarboxylate

methyl 5-(2,4-dichlorophenyl)-4-oxo-2-methyl-2-ethyl-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2-methyl-2-isopropyl-pentanecarboxylate

methyl 5-(2,4-dichlorophenyl)-4-oxo-pentamethylene-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-tetramethylene-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(2,3-benzotetramethylene)-pentanecarboxylate

methyl 5-(2,4-dichlorophenyl)-4-oxo-2,2-hexamethylene-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(2-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(3-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(3-ethylpentamethylene)-pentanecarboxylat

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(3-(1-methylethylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(3-methoxypentamethylene)-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(3-ethoxypentamethylene)-pentanecarboxylate

methyl5-(2,4-dichlorophenyl)-4-oxo-2,2-(2,3-dimethylpentamethylene)-pentanecarboxylate

methyl 5-(2,4-dimethylphenyl)-4-oxo-2,2-dimethyl-pentanecarboxylate

methyl 5-(2,4-dimethylphenyl)-4-oxo-2-methyl-2-ethyl-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2-methyl-2-isopropyl-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-pentamethylene-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-tetramethylene-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(2,3-benzotetramethylene)-pentanecarboxylate

methyl 5-(2,4-dimethylphenyl)-4-oxo-2,2-hexamethylene-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(2-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(3-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(3-ethylpentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(3-(1-methylethyl)pentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(3-methoxypentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(3-ethoxypentamethylene)-pentanecarboxylate

methyl5-(2,4-dimethylphenyl)-4-oxo-2,2-(2,3-dimethylpentamethylene)-pentanecarboxylate

methyl 5-(2,4,6-trimethylphenyl)-4-oxo-2,2-dimethyl-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2-methyl-2-ethyl-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2-methyl-2-isopropyl-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-pentamethylene-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-tetramethylene-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(2,3-benzotetramethylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-hexamethylene-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(2-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(3-methylpentamethylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(3-ethylpentamethylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(3-(1-methylethyl)penta-methylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(3-methoxypentamethylene)-pentanecarboxylate

methyl5-(2,4,6,-trimethylphenyl)-4-oxo-2,2-(3-ethoxypentamethylene)-pentanecarboxylate

methyl5-(2,4,6-trimethylphenyl)-4-oxo-2,2-(2,3-dimethylpentamethylene)-pentanecarboxylate

The active compounds according to the invention are suitable forcontrolling animal pests, preferably arthropods and nematodes, inparticular insects and arachnids, which are encountered in agriculture,in forestry, in the protection of stored products and of materials, andin the hygiene field. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis, Schistocerca gregaria and Supella spp.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp..

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Phthirus spp., Pediculus spp., Haematopinus spp.,Linognathus spp., Solenopotes spp.

From the order of the Mallophaga, for example, Trichodectes spp.,Damalinea spp., Trimenopon spp., Monopon spp., Tinoton spp., Bovicolaspp., Werneckiella spp., Lepikentron spp., Felicola spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp., Panstrongylus spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilussurinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derusspp., Melolontha melolontha, Amphimallon solsti tialis and Costelytrazealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilusspp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp.,Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbiaspp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipulapaludosa, Simulium spp., Eusimulium spp. Phlebotomus spp., Lutzomyiaspp. Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp.,Tabanus spp., Haematopota spp., Philipomyia spp., Bravla spp., Hydrotaeaspp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp.,Glossina spp., Calliphora spp., Wohlfahrlia spp., Sarcophaga spp.,Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp.,Lipoptena spp., Melophagus spp. and Muscina spp.

From the order of the Siphonapterida, for example, Xenopsylla spp.,Ceratophyllus spp., Pulex spp. and Ctenocephalides spp.,

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Myocoptes spp., Otodectesspp., Acarus siro, Argas spp., Ornithodoros spp., Ornithodoros spp.,Dermanyssus spp., Eriophyes ribis, Phyllocoptruta oleivora, Boophilusspp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp.,Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp.,Bryobia praetiosa, Panonychus spp., Tetranychus spp., Dermacentor spp.,Haemaphysalis spp., Raillietia spp., Pneumonyssus spp., Sternostormaspp. and Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example: Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds according to the invention are distinguished by apotent insecticidal and acaricidal activity.

They can be employed particularly successfully for the control ofinsects which are harmful to plants, such as, for example, against thelarvae of the mustard beetle (Phaedon cochleariae) or against the larvaeof the green rice leafhopper (Nephotettix cincticeps) or against thecaterpillars of the cabbage moth (Plutella maculipennis).

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, haulm killers and, especially, asweedkillers. By weeds, in the broadest sense, there are to be understoodall plants which grow in locations where they are undesired. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotola,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena,Secale, Sorghum, Panicum, Sachharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the compounds are suitable for totalweed control, for example on industrial terrain and rail tracks, and onpaths and areas with or without tree stands. Equally, the compounds canbe employed for controlling weeds in perennial crops, for exampleforests, ornamental tree plantings, orchards, vineyards, citrus groves,nut orchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hopfields, in lawns, turf and pastures, and for selectiveweed control in annual crops.

The novel active compounds are highly suitable for selective control ofmonocotyledon weeds in dicotyledon crops, both pre- and post-emergence.For example, they can be used very successfully in cotton or sugar-beetto combat grass weeds.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspoemulsion concentrates,natural and synthetic materials impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If water is used as an extender, organic solvents can, for example, alsobe used as auxiliary solvents. Liquid solvents which are mainly suitableare: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, mineral andvegetable oils, alcohols such as butanol or glycol as well as theirethers and esters, ketones such as acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals such as highly disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam-formers are: for example non-ionic and anionic emulsifiers,such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitabledispersants are: for example lignin-sulphite waste liquors andmethylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes such as gum arabic,polyvinyl alcohol and polyvinyl acetate, or else natural phospholipidssuch as cephalins and lecithins, and synthetic phospholipids can be usedin the formulations. Further additives can be mineral and vegetableoils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematocides, fungicides, growth regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas, substances produced bymicroorganisms and the like.

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl-(E)-2-{2-6-(2-cyanophenoxy)-pyrimidine-4-yloxy!-phenyl}-3-methoxyacrylate;methyl-(E)-methoximino- alpha-(o-tolyloxy)-o-tolyl!acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,chinomethionate, (quinomethionate), chloroneb, chloropicrin,chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole,cyprofuram,

dichlorophen, diclobutrazole, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetylaluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadin, iprobenfos (IBP), iprodione,isoprothiolane,

kasugamycin, copper formulations, such as: copper hydroxide, coppernaphthenate, copper oxychloride, copper sulfate, copper oxide,oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax,myclobutanil,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphene, phthalide, pimaricin,piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon,propamocarb, propiconazole, propineb, pyrazophos, pyrifenox,pyrimethanil, pyroquilon,

quintozene (PCNB),

sulphur and sulphur formulations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxid, trichlamid, tricyclazol,tridemorph, triflumizol, triforin, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinon, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulphate and other copperformulations.

Insecticides/acaricides/nematicides:

abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb,aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,azinphos A, azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, betacyluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezin, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazin,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivemectin,

lamda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, NI 25, nitenpyram,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, primiphos A,profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate,pymetrozin, pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum,pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

RH 5992,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathen, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:

For example anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4 D,2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylaminessuch as, for example, alloxydim, clethodim, cycloxydim, sethoxydim andtralkoxydim; imidazolinones such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example,mefenacet; sulphonylureas such as, for example, amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosufliron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates such as, for example, butylate, cycloate, diallate, EPTC,esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazinessuch as, for example, atrazine, cyanazine, simazine, simetryne,terbutryne and terbutylazine; triazinones such as, for example,hexazinone, metamitron and metribuzin; others such as, for example,aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

The active compound according to the invention can furthermore bepresent in commercially available formulations and in the use forms,prepared from these formulations, as a mixture with synergistic agents.Synergistic agents are compounds which increase the action of the activecompounds, without it being necessary for the synergistic agent added tobe active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an outstanding residual action on wood andclay and by a good stability to alkali on lined substrates.

The active compounds according to the invention act not only againstplant pests, hygiene pests and pests of stored products, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, harvest mites, flies(biting and licking), parasitic fly larvae, lice, hair lice, featherlice and fleas. For example, they display an outstanding activityagainst ticks, such as, for example, Boophilus microplus.

The active compounds of the formula (I) according to the invention arealso suitable for combating arthropods which infest agriculturalproductive livestock such as, for example, cattle, sheep, goats, horses,pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks,geese, bees and other pets, such as, for example, dogs, cats, cage birdsand aquarium fish, and also so-called test animals, such as, forexample, hamsters, guinea pigs, rats and mice. By combating theseanthropods cases of death and reductions in productivity (for meat,milk, wool, hides, eggs, honey, etc.) should be diminished, so that moreeconomic and more simple animal husbandry is possible by use of theactive compounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boli, the feed-through process and suppositories, by parenteraladministration, such as, for example, by injection (intra-muscular,subcutaneous, intravenous, intraperitoneal etc), implants, by nasaladministration, by dermal use in the form, for example, of dipping orbathing, spraying, pouring on and spotting on, washing and powdering,and also with the aid of moulded articles containing the activecompound, such as collars, ear marks, tail marks, limb bands, halters,marking devices, etc.

When used for livestock, poultry, pets etc. the active compounds of theformula (I) can be used as formulations (for example powders, emulsions,free-flowing compositions), which comprise the active compounds in anamount of 1 to 80% by weight, directly or after a 100 to 10,000 folddilution, or they can be used as a chemical bath.

The preparation and the use of the active compounds according to theinvention is illustrated in the following examples.

PREPARATION EXAMPLES Example Ia-1 ##STR212##

1.85 g of potassium tert-butylate are added to a solution of thecompound according to Example II-1 (5.19 g, 15.13 mmol) indimethylformamide (25 ml) and the mixture is stirred at 80° C. for 2hours. 5 ml of acetic acid are added, the mixture is concentrated andthe residue is chromatographed over silica gel (2:1 ethyl acetate:hexane). 3.07 g (65%) of the compound shown above are isolated. Whitesolid, melting point: 219° C.

The compounds of the formula (Ia) listed in Table 14, which are shown inthe form of one of the possible isomers, were prepared analogously or inaccordance with the general instructions of the preparation.

                                      TABLE 14                                    __________________________________________________________________________     ##STR213##                                                                   Ex. No.                                                                            A      B       X   Y   Z.sub.n                                                                           m.p. °C.                               __________________________________________________________________________    Ia-2 (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          H   206                                           Ia-3 (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        255                                           Ia-4                                                                                ##STR214##    CH.sub.3                                                                          CH.sub.3                                                                          H   216                                           Ia-5                                                                                ##STR215##    CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        232                                           Ia-6 (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.3                                                                          6-CH.sub.3                                                                        193                                           Ia-7 (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        248                                           Ia-8 CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          6-CH.sub.3                                                                        248                                           __________________________________________________________________________

Example Ib-1 ##STR216##

Pivaloyl chloride (0.7 ml) is added to a solution of the compoundaccording to Example Ia-1 (936 mg, 3 mmol) in methylene chloride (10 ml)and triethylamine (1 ml). After one hour at room temperature, thereaction mixture is filtered directly over silica gel (mobile phase 1:4,ethyl ether: petroleum ether). 1.1 g (97%) of the compound shown aboveare obtained. White solid, melting point 93° C.

The compounds of the formula (Ib) listed in Table 15, which are shown inthe form of one of the possible isomers, were prepared analogously andin accordance with the general instructions relating to preparation.

                                      TABLE 15                                    __________________________________________________________________________     ##STR217##                                                                   Ex                                   m.p.                                     No.                                                                              A      B       X   Y  Z.sub.n                                                                           R.sup.1 °C.                               __________________________________________________________________________    Ib-2                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   CH.sub.3                                                                              oil                                      Ib-3                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   (CH.sub.3).sub.3 C                                                                    oil                                      Ib-4                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   ClCH.sub.2                                                                            oil                                      Ib-5                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                  ##STR218##                                                                           oil                                      Ib-6                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                              58                                       Ib-7                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.3).sub.3 C                                                                    94                                       Ib-8                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        ClCH.sub.2                                                                            oil                                      Ib-9                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR219##                                                                           oil                                      Ib-10                                                                            (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                  ##STR220##                                                                           oil                                      Ib-11                                                                            (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   CH.sub.3                                                                              68                                       Ib-12                                                                             ##STR221##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                              118                                      Ib-13                                                                             ##STR222##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.3).sub.3 C                                                                    124                                      Ib-14                                                                             ##STR223##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                         ##STR224##                                                                           105                                      Ib-15                                                                             ##STR225##    CH.sub.3                                                                          CH.sub.3                                                                         H   CH.sub.3                                                                              91                                       Ib-16                                                                             ##STR226##    CH.sub.3                                                                          CH.sub.3                                                                         H   (CH.sub.3).sub.3 C                                                                    78                                       Ib-17                                                                             ##STR227##    CH.sub.3                                                                          CH.sub.3                                                                         H                                                                                  ##STR228##                                                                           oil                                      Ib-18                                                                            (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.3).sub.3 C                                                                    103                                      Ib-19                                                                            (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                              105                                      Ib-20                                                                            (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.3).sub.3 C                                                                    112                                      Ib-21                                                                            (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                              115                                      Ib-22                                                                            CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        (CH.sub.3).sub.3 C                                                                    65                                       Ib-23                                                                            CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                              oil                                      __________________________________________________________________________

Example Ic-1: ##STR229##

0.8 ml of ethyl chloroformate is added to a solution of the compoundaccording to Example Ia-1 (1.43 g, 4.58 mmol) in CH₂ Cl₂ (10 ml) andtriethylamine (2 ml) at room temperature. After 2.5 hours, the reactionmixture is filtered directly over silica gel (mobile phase 4:1, CH₂ Cl₂: petroleum ether). 1.37 g (77%) of the compound shown above areobtained as an oil.

¹ HNMR (CDCl₃, 200 MHz, δppm): 3.00 (bs, 1H); 4.28 (q, 2H, J=7 Hz).

The compounds of the formula (Ic) listed in Table 16, which are shown inthe form of one of the possible isomers, were prepared analogously andin accordance with the general instructions relating to preparation.

                                      TABLE 16                                    __________________________________________________________________________     ##STR230##                                                                   Ex.                                  m.p..                                    No.                                                                              A      B       X   Y  Z.sub.n                                                                           M R.sup.2                                                                             °C.                               __________________________________________________________________________    Ic-2                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   O CH.sub.3                                                                            92                                       Ic-3                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   O (CH.sub.3).sub.2 CH                                                                 76                                       Ic-4                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        O CH.sub.3                                                                            100                                      Ic-5                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        O (CH.sub.3).sub.2 CH                                                                 108                                      Ic-6                                                                              ##STR231##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        O (CH.sub.3).sub.2 CH                                                                 161                                      Ic-7                                                                              ##STR232##    CH.sub.3                                                                          CH.sub.3                                                                         H   O (CH.sub.3).sub.2 CH                                                                 63-70                                    Ic-8                                                                             (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.2                                                                         6-CH.sub.3                                                                        O (CH.sub.3).sub.2 CH                                                                 112                                      Ic-9                                                                             (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        O (CH.sub.3).sub.2 CH                                                                 78                                       Ic-10                                                                            CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        O (CH.sub.3).sub.2 CH                                                                 93                                       __________________________________________________________________________

PREPARATION OF THE STARTING COMPOUNDS Example II-1 ##STR233##

A mixture of the compound according to Example XIV-1 (1.95 g; 5.93mnmol), potassium carbonate (0.82 g), acetone (30 ml) and iodomethane (2ml) is boiled under reflux for 5 hours and concentrated and the residueis chromatographed directly over silica gel (mobile phase: 15% of ethylacetate, 85% of petroleum ether). 1.89 g of the compound shown above areobtained as an oil (93%).

¹ HNMR (CDCl₃, 200 MHz, δppm): 2.86 (s, 2H); 3.65 (s, 3H); 3.78 (s, 2H).

The examples of the formula (II) listed in Table 17 were preparedanalogously.

                                      TABLE 17                                    __________________________________________________________________________     ##STR234##                                                                                                   .sup.1 HNMR                                   Ex.-                            (200 MHz, CDCl.sub.3,                         No.                                                                              A      B       X   Y  Z.sub.n                                                                           R.sup.8                                                                          δppm)                                   __________________________________________________________________________    II-2                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         H   CH.sub.3                                                                         2.31(s, 3H); 2.79(m, 2H)                      II-3                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         2.75(s, 2H); 3.67(s, 2H)                      II-4                                                                              ##STR235##    CH.sub.3                                                                          CH.sub.3                                                                         H   CH.sub.3                                                                         2.18(s, 3H); 2.30(s, 3H)                      II-5                                                                              ##STR236##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         2.92(s, 2H); 6.85(s, 2H)                      II-6                                                                             (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         2.16(s, 3H); 2.30(s, 3H); 2.76(s, 2H)         II-7                                                                             (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         0.86(d, 3H, J=7Hz); 2.86(s, 2H)               II-8                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.3                                                                         1.39(s, 6H); 2.68(s, 2H)                      __________________________________________________________________________

Example XIV-1 ##STR237##

A solution of 2,4-dichlorobenzylmagnesium chloride (prepared from 12.6 gof 2,4-dichlorobenzyl chloride and 3 g of magnesium in 100 ml of ethylether) is added to a solution of 10 g of 2,2-pentamethylenesuccinicanhydride (cf.: M. Qudrat-Khuda et al., J. Indian Chem. Soc., (1947),24, 15) in ethyl ether (100 ml) at room temperature. After 30 minutes atroom temperature, 100 ml of water and 20 g of ammonium chloride areadded. The product is extracted with ethyl ether. Chromatography oversilica gel (mobile phase 30% of ethyl acetate: 70% of petroleum ether)gives 3.95 g (22%) of the compound shown above as a white solid ofmelting point 115° C.

Example XIV-2 ##STR238##

A suspension of the compound according to Example (XVII-2) (18.2 g mol)in 20% strength aqueous HCl (300 ml) is heated under reflux for 50hours, cooled and extracted with ethyl ether. After concentration, theresidue is washed with petroleum ether. 9.5 g (65%) of the compoundshown above are obtained as an oil.

The following compounds were prepared analogously to the processdescribed under Example XIV-1 and XIV-2:

                                      TABLE 18                                    __________________________________________________________________________     ##STR239##                                                                                                 .sup.1 HNMR                                     Bx. A      B       X   Y  Z.sub.n                                                                           (200 MHz, CDCl.sub.3,                           No.                           δppm)                                     __________________________________________________________________________    XIV-3                                                                             (CH.sub.2).sub.5                                                                             CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        2.78(s, 2H); 3.69(s, 2H)                        XIV-4                                                                             (CH.sub.2).sub.5                                                                             OCH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        2.30(s, 3H); 2.78 (s, 2H)                       XIV-5                                                                             (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        oil                                             XIV-6                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        oil                                             XIV-7                                                                              ##STR240##    CH.sub.3                                                                          CH.sub.3                                                                         H   oil                                             XIV-8                                                                              ##STR241##    CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        oil                                             __________________________________________________________________________

Example XVII-1 ##STR242##

14.4 g of methyl 2,4,6-trimethylphenylacetate are added to a solution oflithium diisopropylamide (80 mmol) in tetrahydrofuran (100 ml) at -40°C. After 30 minutes at room temperature, 10 g of2,2-pentamethylene-succinic acid methyl ester chloride are added and themixture is stirred at room temperature (1 hour). 100 ml of water and 30g of ammonium chloride are then added. The product is extracted withethyl ether. After concentration, the residue is chromatographed oversilica gel (mobile phase: CH₂ Cl₂). 6.2 g (32%) of a solid of meltingpoint 89° C. are obtained.

The compounds listed in Table 19 were prepared analogously:

                                      TABLE 19                                    __________________________________________________________________________     ##STR243##                                                                                                       .sup.1 HNMR (200 MHz,                     Ex.                                 CDCl.sub.3,                               No. A      B       R.sup.8'                                                                         R.sup.8                                                                          X   Y  Z.sub.n                                                                           δ ppm!)                             __________________________________________________________________________    XVII-2                                                                            (CH.sub.2).sub.5                                                                             CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                         H   2.30 (bs, 6H); 6.9-7.1(m, 3H).            XVII-3                                                                            (CH.sub.2).sub.5                                                                             CH.sub.3                                                                         CH.sub.3                                                                         Cl  Cl H   2.88(m, 2H); 13.12(s, 1H).                XVII-4                                                                             ##STR244##    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        3.66(s, 3H); 3.72(s, 3H).                 XVII-5                                                                            (CH.sub.2).sub.5                                                                             CH.sub.3                                                                         CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                                                         6-CH.sub.3                                                                        6.55(s, 1H); 6.65(s, 1H).                 XVII-6                                                                            (CH.sub.2).sub.2 CHCH.sub.3 (CH.sub.2).sub.2                                                 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        oil                                       XVII-7                                                                            CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                         6-CH.sub.3                                                                        oil                                       XVII-8                                                                             ##STR245##    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                         H   oil                                       __________________________________________________________________________

The compounds of the formulae (XVII) and (XIV) obtained as oils were notcharacterized further, but were employed as crude products in thereactions for the preparation of compounds of the formula (II).

USE EXAMPLES Example A

Tetranychus Test (resistant)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested with alldevelopment stages of the common spider mite or bean spider mite(Tetranychus urticae) are treated by being dipped into the preparationof active compound of the desired concentration.

After the desired time, the destruction in % is determined. 100% meansthat all the spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the compounds according to PreparationExamples Ia-1, Ia-2 and Ia-3 caused a destruction of at least 80% after13 days at an active compound concentration of, for example, 0.01%.

Example B

Phaedon larvae test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae), as long asthe leaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the compounds according to PreparationExamples Ia-1, Ia-2, Ia-3, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-7, Ib-8,Ib-9, Ic-1, Ic-2, Ic-3, Ic-4 and Ic-5 caused a destruction of 100% after7 days at an active compound concentration of, for example, 0.1%.

Example C

Plutella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the diamond-back moth (Plutellamaculipennis) while the leaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the compounds according to PreparationExamples Ia-1, Ia-2, Ia-3, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-7, Ib-8,Ib-9, Ic-1, Ic-2, Ic-3, Ic-4 and Ic-5 caused a destruction of 100% after7 days at an active compound concentration of, for example, 0.1%.

Example D

Spodoptera test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with caterpillars of the owlet moth (Spodoptera frugiperda), aslong as the leaves are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the compounds according to PreparationExamples Ia-2, Ib-2, Ib-3 and Ic-2 caused a destruction of at least 85%after 7 days at an active compound concentration of, for example, 0.1%.

Example E

Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryzae sativa) are treated by being dipped into thepreparation of active compound of the desired concentration and areinfested with larvae of the green rice leafhopper (Nephotettixcincticeps), as long as the seedlings are still moist.

After the desired time, the destruction in % is determined. 100% meansthat all the leafhoppers have been killed; 0% means that none of theleafhoppers have been killed.

In this test, for example, the compounds according to PreparationExamples Ia-2, Ib-2, Ib-3 and Ic-2 caused a destruction of 100% after 6days at an active compound concentration of, for example, 0.1%.

Example F

Myzus Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thepeach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the desired time, the destruction in % is determined. 100% meansthat all the leaf aphids have been killed; 0% means that none of theleaf aphids have been killed.

In this test for example, the compound according to Preparation ExampleIb-7 caused a destruction of 98% after 6 days at an active compoundconcentration of, for example, 0.1%.

Example G

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added, and the concentrate is dilutedwith water to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

In this test, for example, the compound according to Preparation ExampleIa-1 showed, when applied in an amount of, for example, 250 g/ha, goodtolerance by, for example, Beta vulgaris and a degree of damage of atleast 95% with the following test plants: Digitaria sanguinalis,Echinocloa colonom, Panicum miliaceum and Setaria viridis.

Example H

Test with Boophilus microplus resistant/SP-resistant Parkhurst strain

Test animals: Adult satiated females

Solvent: Dimethyl sulphoxide

20 mg of active compound are dissolved in 1 ml of dimethyl sulphoxide,and lower concentrations are prepared by dilution with the same solvent.

The test is carried out as a 5-fold determination. 1 μl of the solutionsis injected into the abdomen and the animals are transferred to dishesand kept in a controlled-environment chamber. The action is determinedby the inhibition of the egg plant. An action of 100% means that no tickhas laid fertile eggs.

In this test, for example, the compounds according to PreparationExamples Ia-1, Ib-6, Ic-4 and Ic-5 in each case showed an action of 100%at an active compound concentration of, for example, 20 μg/animal.

We claim:
 1. Compounds of the formula (I) ##STR246## in which Xrepresents halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Yrepresents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy,alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl orhalogenoalkoxy, Z represents halogen, nitro, cyano, alkyl, alkoxy orhalogenoalkoxy, n represents an integer from 0 to 3, or wherein theradicals X and Z, together with the phenyl radical to which they arebonded, form the naphthalene radical of the formula ##STR247## in whichY has the abovementioned meaning, A and B independently of one anotherrepresent alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, in each case optionally substituted once or severaltimes in an identical or different manner by halogen, or saturated orunsaturated, unsubstituted or substituted cycloalkylor A and B, togetherwith the carbon atom to which they are bonded, form a saturated orunsaturated ring and is optionally substituted, D¹ and D² independentlyof one another represent hydrogen, halogen or alkyl which is optionallysubstituted by halogen of optionally substituted phenyl, G representshydrogen (a), or represents one of the groups ##STR248## E represents ametal ion equivalent or an ammonium ion, L represents oxygen orsulphur,M represents oxygen or sulphur, R¹ represents alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, in each case optionallysubstituted once or several times in an identical or different manner byhalogen, or optionally substituted, saturated or unsaturated cycloalkyl,or represents in each case optionally substituted phenyl, phenylalkyl,phenoxyalkyl R² represents alkyl, alkenyl, alkoxyalkyl orpolyalkoxyalkyl, in each case optionally substituted once or severaltimes in an identical or different manner by halogen, or in each caseoptionally substituted cycloalkyl, phenyl or benzyl, R³ represents alkylwhich is in each case optionally substituted once or several times in anidentical or different manner by halogen, or represents in each caseoptionally substituted phenyl or phenylalkyl, R⁴ and R⁵ independently ofone another represent alkyl, alkoxy, alkylamino, alkenylamino,dialkylamino, dialkenylamino, alkylthio, alkenylthio, alkinylthio orcycloalkylthio, in each case optionally substituted once or severaltimes in an identical or different manner by halogen, or represent ineach case optionally substituted phenyl, phenoxy or phenylthio, R⁶ andR⁷ independently of one another represent hydrogen or alkyl, alkenyl,alkoxy or alkoxyalkyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, orrepresent optionally substituted phenyl or represent optionallysubstituted benzyl, orR⁶ and R⁷ together represent an alkyleneradicaland the enantiomerically pure forms of compounds or the formula(I).
 2. Compounds of the formula (I) according to claim 1, which,incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g)of the group G, have the following structures (Ia) to (Ig): ##STR249##wherein A, B, D¹, D², E, L, M, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and nhave the meanings given in claim
 1. 3. Compounds or the formula (I)according to claim 1, in whichX represents halogen, nitro, cyano, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulphinyl, C₁ -C₆ -alkylsulphonyl, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy, Y represents hydrogen, halogen, nitro, cyano, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₆ -alkylthio, C₁ -C₆-alkylsulphinyl, C₁ -C₆ -alkylsulphonyl, C₁ -C₃ -halogenoalkyl or C₁ -C₃-halogenoalkoxy, Z represents halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁-C₆ -alkoxy or C₁ -C₃ -halogenoalkoxy, represents 0, 1, 2 or 3,or theradicals X and Z, together with the phenyl radical to which they arebonded, represent the naphthalene radical of the formula ##STR250## inwhich Y has the abovementioned meaning, A and B independently of oneanother represent C₁ -C₁₂ -alkyl, C₃ -C₈ -alkenyl, C₃ -C₈ -alkinyl, C₁-C₁₀ -alkoxy-C₁ -C₈ -alkyl, poly-C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl or C₁ -C₁₀-alkylthio-C₁ -C₈ -alkyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, orsaturated or unsaturated cycloalkyl which has 3 to 8 ring aroma, isoptionally substituted once or several times in an identical ordifferent manner by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxyor A and B,together with the carbon atom to which they are bonded, form a saturatedor unsaturated 3- to 8-membered ring and is optionally substituted onceor several times in an identical or different manner by halogen, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio, or Aor B, together with the carbon atom to which they are bonded, representC₃ -C₈ -cycloalkyl, in which substituents, together with the carbonatoms to which they are bonded, represent a saturated or unsaturated 5-to 7-membered ring which is optionally substituted once or several timesin an identical or different manner by halogen, C₁ -C₆ -alkyl or C₁ -C₆-alkoxy D¹ and D² independently of one another represent hydrogen,halogen or C₁ -C₆ -alkyl which is optionally substituted once or severaltimes in an identical or different manner by halogen, or representphenyl which is optionally substituted once or several times in anidentical or different manner by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy,nitro, C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy, G representshydrogen (a), or represents one of the groups ##STR251## in which Erepresents a metal ion equivalent or an ammonium ion,L represents oxygenor sulphur, M represents oxygen or sulphur, R¹ represents C₁ -C₂₀-alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl, C₁ -C₈-alkylthio-C₁ -C₈ -alkyl or poly-C₁ -C₈ -alkoxy-C₁ -C₈ -alkyl, in eachcase optionally substituted once or several times in an identical ordifferent manner by halogen, or saturated or unsaturated cycloalkylhaving 3 to 8 ring atoms, which is optionally substituted once orseveral times in an identical or different manner by halogen, C₁ -C₆-alkyl or C₁ -C₆ -alkoxy or represents phenyl which is optionallysubstituted once or several times in an identical or different manner byhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-halogenoalkyl or C₁ -C₆ -halogenoalkoxy, or represents phenyl-C₁ -C₆-alkyl which is optionally substituted once or several times in anidentical or different manner by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy,C₁ -C₆ -halogenoalkyl or C₁ -C₆ -halogenoalkoxy, or represents hetarylwhich has 5 or 6 ring atoms and is optionally substituted once orseveral times in an identical or different manner by halogen or C₁ -C₆-alkyl, or represents phenoxy-C₁ -C₆ -alkyl which is optionallysubstituted once or several times in an identical or different manner byhalogen or C₁ -C₆ -alkyl, or represents hetaryloxy-C₁ -C₆ -alkyl whichhas 5 or 6 ring atoms and is optionally substituted once or severaltimes in an identical or different manner by halogen, amino or C₁ -C₆-alkyl, R² represents C₁ -C₂₀ -alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈-alkoxy-C₂ -C₈ -alkyl or poly-C₁ -C₂₀ -alkoxy-C₂ -C₈ -alkyl, in eachcase optionally substituted once or several times in an identical ordifferent manner by halogen, or represents C₃ -C₈ -cycloalkyl which isoptionally substituted once or several times in an identical ordifferent manner by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy, orrepresents phenyl or benzyl, in each case optionally substituted once orseveral times in an identical or different manner by halogen, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₆ -halogenoalkyl,represents C₁ -C₁₂ -alkyl which is in each case optionally substitutedonce or several times in an identically or different manner by halogen,or represents phenyl or phenyl-C₁ -C₄ -alkyl, in each case optionallysubstituted once or several times in an identically or different mannerby halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₃ -halogenoalkyl, C₁ -C₃-halogenoalkoxy, cyano or nitro, R⁴ and R⁵ independently of one anotherrepresent C₁ -C₈ -alkyl, C₁ -C₈ -alkoxy, C₁ -C₈ -alkylamino, C₃ -C₈-alkenylamino, di-(C₁ -C₈ -alkyl)-amino, di-(C₃ -C₈ -alkenyl)-amino, C₁-C₈ -alkylthio, C₃ -C₅ -alkenylthio, C₃ -C₅ -alkinylthio or C₃ -C₇-cycloalkylthio, in each case optionally substituted once or severaltimes in an identical or different manner by halogen, or representphenyl, phenoxy or phenylthio, in each case optionally substitute onceor several times in an identically or different manner by halogen,nitro, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -halogenoalkylthio, C₁ -C₄ -alkyl or C₁ -C₄ -halogenoalkyl and R⁶and R⁷ independently of one another represent hydrogen, or represent C₁-C₁₀ -alkyl, C₁ -C₁₀ -alkoxy, C₃ -C₈ -alkenyl or C₁ -C₁₀ -alkoxy-C₁ -C₁₀-alkyl, in each case optionally substituted once or several times in anidentical or different manner by halogen, or represent phenyl which isoptionally substituted once or several times in an identical ordifferent manner by halogen,C₁ -C₃ -halogenoalkyl, C₁ -C₈ -alkyl or C₁-C₈ -alkoxy, or represent benzyl which is optionally substituted once orseveral times in an identical or different manner by halogen, C₁ -C₈-alkyl, C₁ -C₈ -halogenoalkyl or C₁ -C₈ -alkoxy, or together represent aC₂ -C₆ -alkylene radical,and the enantiomerically pure forms ofcompounds of the formula (I).
 4. Compounds of the formula (I) accordingto claim 1, in whichX represents fluorine, chlorine, bromine, nitro,cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₂ -halogenoalkyl or C₁ -C₂-halogenoalkoxy, Y represents hydrogen, fluorine, chlorine, bromine,nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₂ -halogenoalkyl or C₁-C₂ -halogenoalkoxy, Z represents fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₂ -halogenoalkoxy, nrepresents 0, 1 or 2, A and B independently of one another represent C₁-C₁₀ -alkyl, C₃ -C₆ -alkinyl, C₁ -C₈ -alkoxy-C₁ -C₆ -alkyl, poly-C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₈ -alkylthio-C₁ -C₆ -alkyl, in each caseoptionally substituted once to five times in an identical or differentmanner by fluorine or chlorine, or saturated or unsaturated cycloalkylwhich has 3 to 7 ring atoms, is optionally substituted once to threetimes in an identical or different manner by fluorine, chlorine, C₁ -C₄-alkyl or C₁ -C₄ -alkoxy,or A and B, together with the carbon atom towhich they are bonded, form a saturated or unsaturated 3 to 7-memberedring and is optionally substituted once to three times in an identicalor different manner by fluorine, chlorine, C₁ -C₅ -alkyl, C₁ -C₅-alkoxy, C₁ -C₃ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy, C₁ -C₃-alkylthioor A and B, together with the carbon atom to which they arebonded, represent C₄ -C₇ -cycloalkyl, in which two substituents,together with the carbon atoms to which they are bonded, represent asaturated or unsaturated 5- or 6-membered ring which is optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, C₁ -C₃ -alkyl or C₁ -C₃ -alkoxy D¹ and D²independently of one another represent hydrogen, fluorine, chlorine orC₁ -C₄ -alkyl which is optionally substituted once to five times in anidentical or different manner by fluorine or chlorine, or representphenyl which is optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, nitro, C₁ -C₂ -halogenoalkyl or C₁ -C₂-halogenoalkoxy, G represents hydrogen (a), or represents one of thegroups ##STR252## in which E represents a metal ion equivalent or anammonium ion,L represents oxygen or sulphur, M represents oxygen orsulphur, R¹ represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl or poly-C₁ -C₆-alkoxy-C₂ -C₆ -alkyl, in each case optionally substituted once to ninetimes in an identical or different manner by halogen, or cycloalkylwhich has 3 to 7 ring atoms, is optionally substituted once or six timesin an identical or different manner by fluorine,chlorine, C₁ -C₄ -alkylor C₁ -C₄ -alkoxy, or represents phenyl which is optionally substitutedonce to three times in an identical or different manner by fluorine,chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃-halogenoalkoxy, or represents phenyl-C₁ -C₄ -alkyl which is optionallysubstituted once to three times in an identical or different manner byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃-halogenoalkyl or C₁ -C₃ -halogenoalkoxy, or represents phenoxy-C₁ -C₅-alkyl which is optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, bromine or C₁ -C₄-alkyl, R² represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl, C₁ -C₆-alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, in each caseoptionally substituted once to nine times in an identical or differentmanner by fluorine or chlorine, or represents C₃ -C₇ -cycloalkyl whichis optionally substituted once to five times in an identical ordifferent manner by fluorine, chlorine, C₁ -C₄ -alkoxy, or representsphenyl or benzyl, in each case optionally substituted once to threetimes in an identical or different manner by fluorine, chlorine,bromine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₃ -alkoxy or C₁ -C₃-halogenoalkyl, R³ represents C₁ -C₆ -alkyl which is in each caseoptionally substituted once to five times in an identical or differentmanner by fluorine or chlorine, or represents phenyl or phenyl-C₁ -C₂-alkyl, in each case optionally substituted once to three times in anidentical or different manner by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -halogenoalkoxy,cyano or nitro, R⁴ and R⁵ independently of one another represent C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylamino, C₃ -C₆ -alkenylamino, di-(C₁-C₆ -alkyl)-amino, di-(C₃ -C₆ -alkenyl)-amino, C₁ -C₆ -alkylthio, C₃ -C₄-alkenylthio, C₃ -C₄ -alkinylthio or C₃ -C₆ -cycloalkylthio, in eachcase optionally substitute once to five times in an identical ordifferent manner by fluorine or chlorine, or represent phenyl, phenoxyor phenylthio, in each case optionally substitute once to three times inan identical or different manner by fluorine, chlorine, bromine, nitro,cyano, C₁ -C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-halogenoalkylthio, C₁ -C₃ -alkyl or C₁ -C₃ -halogenoalkyl and R⁶ and R⁷independently of one another represent hydrogen, or represent C₁ -C₆-alkyl, C₁ -C₆ -alkoxy C₃ -C₆ -alkenyl or C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl,in each case optionally substituted once to five times in an identicalor different manner by fluorine or chlorine, or represent phenyl whichis optionally substituted once to three times in an identical ordifferent manner by fluorine, chlorine, C₁ -C₃ -halogenoalkyl, C₁ -C₃-alkyl or C₁ -C₃ -alkoxy, or represent benzyl which is optionallysubstituted once to five times in an identical or different manner byfluorine, chlorine, C₁ -C₃ -alkyl, C₁ -C₃ -halogenoalkyl or C₁ -C₃-alkoxy, or together represent a C₄ -C₆ -alkylene radical,and theenantiomerically pure forms of compounds of the formula (I). 5.Compounds of the formula (I) according to claim 1, in whichX representsfluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-propyl,i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy or chlorodifluoromethoxy, Y represents hydrogen,fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, orchlorodifluoromethoxy, Z represents fluorine, chlorine, bromine, nitro,cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl,methoxy, ethoxy, trifluoromethyl, difluoromethoxy, orchlorodifluoromethoxy, n represents 0 or 1, A and B independently of oneanother represent C₁ -C₈ -alkyl, C₃ -C₄ -alkenyl, C₃ -C₄ -alkinyl, C₁-C₆ -alkoxy-C₁ -C₄ -alkyl, poly-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₆-alkylthio-C₁ -C₄ -alkyl, in each case optionally substituted once tothree times in an identical or different manner by fluorine or chlorine,or cycloalkyl which has 3 to 6 ring atoms, is optionally substitutedonce or twice in an identical or different manner by fluorine, chlorine,methyl, ethyl, methoxy, or ethoxy,or A and B, together with the carbonatom to which they are bonded, form a saturated or unsaturated 3- to6-membered ring and is optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, trifluoromethyl, C₁ -C₂ -alkylthio or A and B, togetherwith the carbon atom to which they are bonded, represent C₅ -C₆-cycloalkyl, in which two substituents, together with the carbon atomsto which they are bonded, represent a saturated or unsaturated 5- or6-membered ring which is optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, methyl, ethyl,methoxy or ethoxy D¹ and D² independently of one another representhydrogen, fluorine, chlorine, methyl or ethyl, or represent phenyl whichis optionally substituted once or twice in an identical or differentmanner by fluorine, chlorine, methyl, methoxy or trifluoromethyl, Grepresents hydrogen (a), or represents one or the groups ##STR253## inwhich E represents a metal ion equivalent or an ammonium ion,Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents C₁ -C₁₄ -alkyl, C₂ -C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₆-alkyl, C₁ -C₄ -alkylthio-C₁ -C₆ -alkyl or poly-C₁ -C₄ -alkoxy-C₂ -C₄-alkyl, in each case optionally substituted once to three times in anidentical or different manner by fluorine or chlorine, or cycloalkylwhich has 3 to 6 ring atoms, is optionally substituted once or twice inan identical or different manner by fluorine, chlorine, methyl, ethyl,methoxy or ethoxy, or represents phenyl which is optionally substitutedonce or twice in an identical or different manner by fluorine, chlorine,bromine, methyl, ethyl, propyl, i-propyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, or represents phenyl-C₁ -C₃ -alkyl, inparticular benzyl, which is optionally substituted once or twice in anidentical or different manner by fluorine, chlorine, bromine, methyl,ethyl, propyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, or represents phenoxy-C₁ -C₄ -alkyl which isoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, methyl or ethyl, R² represents C₁ -C₁₄ -alkyl-C₂-C₁₄ -alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₄ -alkoxy-C₂-C₆ -alkyl, in each case optionally substituted once to five times in anidentical or different manner by fluorine or chlorine, or represents C₃-C₆ -cycloalkyl which is optionally substituted once to three times inan identical or different manner by fluorine, chlorine, methyl, ethyl,methoxy or ethoxy, or represents phenyl or benzyl, in each caseoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, nitro, cyano, methyl, ethyl, propyl, i-propyl,methoxy, ethoxy or trifluoromethyl, R³ represents C₁ -C₆ -alkyl which isoptionally substituted once to three times in an identical or differentmanner by fluorine or chlorine, or represents phenyl or benzyl, in eachcase optionally substituted once or twice in an identical or differentmanner by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R⁴ and R⁵ independently of one anotherof one another represent C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-alkylamino, C₃ -C₄ -alkenylamino, di-(C₁ -C₄ -alkyl)-amino, di-(C₃ -C₄-alkenyl)-amino, C₁ -C₄ -alkylthio, in each case optionally substitutedonce to three times in an identical or different manner by fluorine orchlorine, or represent phenyl, phenoxy or phenylthio, in each caseoptionally substituted once or twice in an identical or different mannerby fluorine, chlorine, bromine, nitro, cyano, C₁ -C₂ -alkoxy, C₁ -C₂-fluoroalkoxy, C₁ -C₂ -choroalkoxy, C₁ -C₂ -alkylthio, C₁ -C₂-fluoroalkylthio, C₁ -C₂ -chloroalkylthio or C₁ -C₃ -alkyl, R⁶ and R⁷independently of one another represent hydrogen, or represent C₁ -C₄-alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, in each caseoptionally substituted once to three times in an identical or differentmanner by fluorine or chlorine, or represent phenyl which is optionallysubstituted once or twice in an identical or different manner byfluorine, chlorine, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -alkyl or C₁ -C₂-alkoxy, or represent benzyl which is optionally substituted once ortwice in an identical or different manner by fluorine, chlorine,bromine, C₁ -C₂ -alkyl, C₁ -C₂ -halogenoalkyl or C₁ -C₂ -alkoxy, ortogether represent a C₄ -C₆ -alkylene radical,and the enantiomericallypure forms of compounds of the formula (I).
 6. Process for thepreparation of compounds of the formula (I) according to claim 1, whichcomprises(A)to prepare compounds of the formula (Ia) ##STR254## in whichA, B, D¹, D², X, Y, Z and n have the meaning given in claim 1,ketocarboxylic acid esters of the formula (II) ##STR255## in which A, B,D¹, D², X, Y, Z and n have the abovementioned meaning andR⁸ representsalkyl, are subjected to intermolecular cyclization, if appropriate inthe presence of a diluent and in the presence of a base, and (B)toprepare compounds of the formula (Ib) ##STR256## in which A, B, D¹, D²,X, Y, Z, R¹ and n have the meaning given in claim 1, compounds of theformula (Ia) ##STR257## in which A, B, D¹, D², X, Y, Z and n have theabovementioned meaning, α) are reacted with acid halides of the formula(III) ##STR258## in which R¹ has the abovementioned meaning andHalrepresents halogen, if appropriate in the presence of a diluent and ifappropriate in the presence of an acid-binding agent, or β) are reactedwith carboxylic acid anhydrides of the formula (IV)

    R.sup.1 --CO--O--CO--R.sup.1                               (IV)

in whichR¹ has the abovementioned meaning, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent,and (C)to prepare compounds of the formula (Ic)##STR259## in which A, B, D¹, D², X, Y, Z, R² and n have the meaninggiven in claim 1,L represents oxygen and M represents oxygen or sulphur,compounds of the formula (Ia) ##STR260## in which A, B, D¹, D², X, Y, Zand n have the abovementioned meaning, are reacted with a chloroformicacid ester or chloroformic acid thiol ester of the formula (V)

    R.sup.2 --M--CO--Cl                                        (V)

in whichR² and M have the abovementioned meaning, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent, and (D)to prepare compounds of the formula (Ic)##STR261## in which A, B, D¹, D², R², X, Y, Z and n have theabovementioned meaning,L represents sulphur and M represents oxygen orsulphur, compounds of the formula (Ia) ##STR262## in which A, B, D¹, D²,X Y, Z and n have the abovementioned meaning, α) are reacted with achloromonothioformic acid ester or chlorodithioformic acid ester of theformula (VI) ##STR263## in which M and R² have the abovementionedmeaning, if appropriate in the presence of a diluent and if appropriatein the presence of an acid-binding agent, or β) are reacted with carbondisulphide and then with alkyl halides of the formula (VII)

    R.sup.2 -Hal                                               (VII)

in whichR² has the abovementioned meaning andHal represents chlorine,bromine or iodine, if appropriate in the presence of a diluent and ifappropriate in the presence of a base, and (E)to prepare compounds ofthe formula (Id) ##STR264## in which A, B, D¹, D², X, Y, Z, R³ and nhave the meaning given in claim 1, compounds of the formula (Ia)##STR265## in which A, B, D¹, D², X, Y, Z and n have the abovementionedmeaning, are reacted with sulphonic acid chlorides of the formula (VIII)

    R.sup.3 --SO.sub.2 --Cl                                    (VIII)

in whichR³ has the abovementioned meaning, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent, and (F)to prepare compounds of the formula (Ie)##STR266## in which A, B, D¹, D², L, X, Y, Z, R⁴, R⁵ and n have themeaning given in claim compounds of the formula (Ia) ##STR267## in whichA, B, D¹, D², X, Y, Z and n have the abovementioned meaning, are reactedwith phosphorus compounds of the formula (IX) ##STR268## in which L, R⁴and R⁵ have the abovementioned meaning andHal represents halogen, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent, and (G)to prepare compounds of theformula (If) ##STR269## in which A, B, D¹, D², L, X, Y, Z, R⁶, R⁷ and nhave the meaning given in claim 1, compounds of the formula (Ia)##STR270## in which A, B, D¹, D², X, Y, Z and n have the abovementionedmeaning, α) are reacted with isocyanates or isothiocyanates of theformula (X)

    R.sup.6 --N═C═L                                    (X)

in whichR⁶ and L have the abovementioned meaning, if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or β) are reacted with carbamic acid chlorides or thiocarbamic acidchlorides of the formula (XI) ##STR271## in which L, R⁶ and R⁷ have theabovementioned meaning, if appropriate in the presence of a diluent andif appropriate in the presence of an acid-binding agent, and (H)toprepare compounds of the formula (Ig) ##STR272## in which X, Y, D¹, D²,Z, A, B and n have the abovementioned meaning andE represents a metalion equivalent or an ammonium ion, compounds of the formula (Ia)##STR273## in which X, Y, Z, A, B, D¹, D² and n have the abovementionedmeaning, are reacted with metal compounds of the formula (XII) or aminesof the formula (XIII) ##STR274## in which Me represents mono- ordivalent metal ions andt represents the number 1 or 2 and R⁹, R¹⁰ andR¹¹ independently of one another represent hydrogen, alkyl, alkoxy orhydroxyl, if appropriate in the presence of a diluent.
 7. Aninsecticidal composition comprising an insecticidally effective amountof a compound according to claim 1 and an extender.
 8. A method ofcontrolling unwanted insects which comprises administering to suchinsects or to a locus from which it is desired to exclude such insectsan insecticidally effective amount of a compound according to claim 1.9. An herbicidal composition comprising an herbicidally effective amountof a compound according to claim 1 and an extender.
 10. A method ofcontrolling unwanted vegetation which comprises applying to suchvegetation or to a locus for which it is desired to exclude suchvegetation an herbicidally effective amount of a compound according toclaim 1.